Imidazolidinone derivatives

ABSTRACT

A compound of the formula (IA) or (IB)  
                 
 
     wherein  
     G 1 , G 2 , G 3  and G 4  are independently of one another C 1 -C 18 alkyl or C 5 -C 12 cycloalkyl or the radicals G 1  and G 2  and the radicals G 3  and G 4  form independently of one another, together with the carbon atom they are attached to, C 5 -C 12 cycloalkyl;  
     R is hydrogen C 1 -C 18 alkyl, C 1 -C 18 hydroxyalkyl, C 2 -C 18 alkenyl, C 5 -C 12 cycloalkyl, C 7 -C 12 phenylalkyl unsubstituted or substituted on the phenyl radical by C 1 -C 4 alkyl and/or C 1 -C 4 alkoxy; or C 1 -C 18 alkanoyl;  
     R* is hydrogen, C 1 -C 18 alkyl, oxyl, —OH, —CH 2 CN, C 3 -C 6 alkenyl, C 3 -C 8 alkynyl, C 7 -C 12 phenylalkyl unsubstituted or substituted on the phenyl radical by C 1 -C 4 alkyl and/or C 1 -C 4 alkoxy; C 1 -C 8 acyl, C 1 -C 18 alkoxy, C 1 -C 18 hydroxyalkoxy, C 2 -C 18 alkenyloxy, C 5 -C 12 cycloalkoxy, C 7 -C 12 phenylalkoxy unsubstituted or substituted on the phenyl radical by C 1 -C 4 alkyl and/or C 1 -C 4 alkoxy; C 1 -C 18 alkanoyloxy, (C 1 -C 18 alkoxy)carbonyl, glycidyl or a group —CH 2 CH(OH)(G) with G being hydrogen, methyl or phenyl;  
     n is 1, 2, 3 or  4;    
     n* is 1, 2 or 3;  
     X is an organic radical of a valency equal to n; and  
     X* is a triazinic radical with a valency equal to n*;  
     with the proviso that when n is 1, R is methyl, ethyl, propyl, C 1 -C 18 hydroxyalkyl, C 2 -C 18 alkenyl, C 5 -C 12 cycloalkyl or C 1 -C 18 alkanoyl.  
     The compounds described above are useful for stabilizing an organic material against degradation induced by light, heat or oxidation.

[0001] The present invention relates to particular imidazolidinonederivatives, to their use as light stabilizers, heat stabilizers andoxidation stabilizers for organic materials, particularly syntheticpolymers, and to the organic materials thus stabilized.

[0002] Some imidazolidinone derivatives are for example disclosed inDE-A-2,621,947, U.S. Pat. No. 3,532,703, U.S. Pat. No. 3,971,757,WO-A-98/30601 and U.S. Pat. No. 4,448,969.

[0003] The present invention relates in particular to

[0004] a compound of the formula (IA) or (IB)

[0005] wherein

[0006] G₁, G₂, G₃ and G₄ are independently of one another C₁-C₁₈alkyl orC₅-C₁₂cycloalkyl or the radicals G₁ and G₂ and the radicals G₃ and G₄form independently of one another, together with the carbon atom theyare attached to, C₅-C₁₂cycloalkyl;

[0007] R is C₁-C₁₈alkyl, C₁-C₁₈hydroxyalkyl, C₂-C₁₈alkenyl,C₅-C₁₂cycloalkyl, C₇-C₁₂phenylalkyl unsubstituted or substituted on thephenyl radical by C₁-C₄alkyl and/or C₁-C₄alkoxy; or C₁-C₁₈alkanoyl;

[0008] R* is hydrogen, C₁-C₁₈alkyl, oxyl, —OH, —CH₂CN, C₃-C₆alkenyl,C₃-C₈alkynyl, C₇-C₁₂phenylalkyl unsubstituted or substituted on thephenyl radical by C₁-C₄alkyl and/or C₁-C₄alkoxy; C₁-C₈acyl,C₁-C₁₈alkoxy, C₁-C₁₈hydroxyalkoxy, C₂-C₁₈alkenyloxy, C₅-C₁₂cycloalkoxy,C₇-C₁₂phenylalkoxy unsubstituted or substituted on the phenyl radical byC₁-C₄alkyl and/or C₁-C₄alkoxy; C₁-C₁₈alkanoyloxy,(C₁-C₁₈alkoxy)carbonyl, glycidyl or a group —CH₂CH(OH)(G) with G beinghydrogen, methyl or phenyl;

[0009] n is 1, 2, 3 or 4;

[0010] n* is 1, 2 or 3;

[0011] X is an organic radical of a valency equal to n;

[0012] when n* is 1, X* is a group of the formula (IB-1)

[0013] wherein

[0014] Z₁* and Z₂* are independently of one another —O— or >N—R₃*;

[0015] R₁*, R₂* and R₃* are independently of one another hydrogen,C₁-C₁₈alkyl, C₃-C₁₈alkenyl, C₅-C₁₂cycloalkyl which is unsubstituted orsubstituted by C₁-C₄alkyl and/or C₁-C₄alkoxy; or C₇-C₉phenylalkyl whichis unsubstituted or substituted on the phenyl radical by C₁-C₄alkyland/or C₁-C₄alkoxy;

[0016] when n* is 2, X* is a group of the formula (IB-2)

[0017] wherein Z₁* and R,* are as defined above;

[0018] when n* is 3, X* is a group of the formula (IB-3);

[0019] when n is 2, 3 or 4, each of the radicals G₁, G₂, G₃, G₄ and Rcan have the same or a different meaning in the units of the formula

[0020] when n* is 2 or 3, each of the radicals G₁, G₂, G₃, G₄ and R* canhave the same or a different meaning in the units of the formula

[0021] with the proviso that when n is 1, R is methyl, ethyl, propyl,C₁-C₁₈hydroxyalkyl, C₂-C₁₈alkenyl, C₅-C₁₂cycloalkyl or C₁-C₁₈alkanoyl.

[0022] A preferred embodiment relates to a compound of the formula (IA)wherein when n is 1, X is C₂-C₁₈alkyl, C₂-C₁₈hydroxyalkyl, C₂-C₁₈alkylinterrupted by oxygen, sulphur or >N—R₀ with R₀ being as defined below;C₂-C₁₈alkenyl, C₂-C₁₈alkynyl, C₅-C₁₂cycloalkyl unsubstituted orsubstituted by —OH, C₁-C₄alkyl and/or C₁-C₄alkoxy; phenyl orC₇-C₉phenylalkyl unsubstituted or substituted on the phenyl radical by—OH, C₁-C₄alkyl and/or C₁-C₄alkoxy; or X is one of the groups of theformulae (II-a) to (II-m)

[0023] Y₁, Y₂, Y₅, Y₆, Y₇ and Y₉ are a direct bond, C₁-C₁₂alkylene,C₅-C₁₂cycloalkylene or phenylene;

[0024] Y₃, Y₄, Y₈, Y₁₀, Y₁, and Y₁₂ are C₂-C₁₂alkylene,C₅-C₁₂cycloalkylene or phenylene;

[0025] R₁, R₂, R₃, R₄, R₅, R₆, R₇ and R₁₃ are hydrogen, C₁-C₁₈alkyl,C₂-C₁₈alkyl interrupted by oxygen, sulphur or >N—R₀ with R₀ being asdefined below; C₂-C₁₈alkenyl, C₂-C₁₈alkynyl, C₅-C₁₂cycloalkylunsubstituted or substituted by C₁-C₄alkyl and/or C₁-C₄alkoxy; phenylunsubstituted or substituted by C₁-C₄alkyl and/or C₁-C₄alkoxy; orC₇-C₉phenylalkyl unsubstituted or substituted on the phenyl radical byC₁-C₄alkyl and/or C₁-C₄alkoxy;

[0026] Z₁, Z₂ and Z₃ are independently of one another —O— or >N—R₁₆;

[0027] R₀, R₈, R₉, R₁₀, R₁₁, R₁₂, R₁₄, R₁₅ and R₁₆ are independently ofone another hydrogen, C₁-C₁₈alkyl, C₃-C₁₈alkenyl, C₅-C₁₂cycloalkyl whichis unsubstituted or substituted by C₁-C₄alkyl and/or C₁-C₄alkoxy; orC₇-C₉phenylalkyl which is unsubstituted or substituted on the phenylradical by C₁-C₄alkyl and/or C₁-C₄alkoxy;

[0028] with the proviso that the formula (II-b) is different fromethoxycarbonyl;

[0029] when n is 2, X is C₂-C₁₂alkylene, C₂-C₁₆alkylene interrupted byoxygen, sulphur or >N—R₀′ with R₀′ being as defined below;C₂-C₁₂alkenylene, C₂-C₁₂alkynylene, C₅-C₁₂cycloalkylene,C₅-C₁₂cycloalkylene-(C₁-C₄alkylene)-C₅-C₁₂cycloalkylene,C₁-C₄alkylene-(C₅-C₁₂cycloalkylene)-C₁-C₄alkylene, phenylene,phenylene-(C₁-C₄alkylene)-phenylene orC₁-C₄alkylene-phenylene-C₁-C₄alkylene, or X is one of the groups of theformulae (III-a) to (III-j)

[0030] Y₁′, Y₁″, Y₂′, Y₂″, Y₅′, Y₅″, Y₆′, Y₆″, Y₇′ and Y₇″ areindependently of one another a direct bond, C₁-C₁₂alkylene,C₅-C₁₂cycloalkylene or phenylene;

[0031] Y₃′, Y₃″, Y₄′, Y₄″, Y₈′, Y₈″, Y₁₁′,Y₁₁″, Y₁₂′ and Y₁₂″ areindependently of one another C₂-C₁₂alkylene, C₅-C₁₂cycloalkylene orphenylene;

[0032] A₁, A₂, A₃, A₄, A₅, A₆, A₇, A₈ and A₉ are C₂-C₁₂alkylene,C₂-C₁₂alkylene interrupted by oxygen, sulphur or >N—R₀′ with R₀′ beingas defined below, C₂-C₁₂alkenylene, C₂-C₁₂alkynylene,C₅-C₁₂cycloalkylene,C₅-C₁₂cycloalkylene-(C₁-C₄alkylene)-C₅-C₁₂cycloalkylene,C₁-C₄alkylene-(C₅-C₁₂cycloalkylene)-C₁-C₄alkylene, phenylene,phenylene-(C₁-C₄alkylene)-phenylene orC₁-C₄alkylene-phenylene-C₁-C₄alkylene; and A₁ and A₅ are additionally adirect bond;

[0033] Z₁′, Z₂′ and Z₃′ are independently of one another —O— or >N—R₁₆′;and

[0034] R₀′, R₁₄′ and R₁₆′ are independently of one another hydrogen,C₁-C₁₈alkyl, C₃-C₁₈alkenyl, C₅-C₁₂cycloalkyl which is unsubstituted orsubstituted by C₁-C₄alkyl and/or C₁-C₄alkoxy; or C₇-C₉phenylalkyl whichis unsubstituted or substituted on the phenyl radical by C₁-C₄alkyland/or C₁-C₄alkoxy:

[0035] when n is 3, X is C₅-C₂₅alkantriyl, C₄-C₁₈triacyl or a group ofthe formula (IV);

[0036] Y₁₃′, Y₁₃″ and Y₁₃′″ are independently of one anotherC₂-C₁₂alkylene, C₅-C₁₂cycloalkylene or phenylene;

[0037] Z₁″, Z₂″ and Z₃″ are independently of one another —O— or >N—R₁₆″;and R₁₆″ is hydrogen, C₁-C₁₈alkyl, C₃-C₁₈alkenyl, C₅-C₁₂cycloalkyl whichis unsubstituted or substituted by C₁-C₄alkyl and/or C₁-C₄alkoxy; orC₇-C₉phenylalkyl which is unsubstituted or substituted on the phenylradical by C₁-C₄alkyl and/or C₁-C₄alkoxy; and

[0038] when n is 4, X is C₅-C₂₀alkantetrayl, C₆-C₂₂tetraacyl or a groupof the formula (V)

[0039] Y₁₄′ and Y₁₄″ are independently of one another C₂-C₁₂alkylene,C₅-C₁₂cycloalkylene or phenylene;

[0040] Z₁′″, Z₂′″, M and T are independently of one another —O— or>N—R₁₆′″, and M and T are additionally —S—;

[0041] R₁₆′″ is hydrogen, C₁-C₁₈alkyl, C₃-C₁₈alkenyl, C₅-C₁₂cycloalkylwhich is unsubstituted or substituted by C₁-C₄alkyl and/or C₁-C₄alkoxy;or C₇-C₉phenylalkyl which is unsubstituted or substituted on the phenylradical by C₁-C₄alkyl and/or C₁-C₄alkoxy; and q is an integer from 2 to12.

[0042] X as an organic radical of a valency equal to n may be forexample an aliphatic, cycloaliphatic or aromatic residue optionallycontaining a heteroatom such as oxygen, sulphur or nitrogen.

[0043] Examples of alkyl containing not more than 18 carbon atoms aremethyl, ethyl, propyl, isopropyl, butyl, 2-butyl, isobutyl, t-butyl,pentyl, 2-pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, t-octyl, nonyl,decyl, undecyl, dodecyl, tridecyl, tetradecyl, hexadecyl and octadecyl.G₁, G₂, G₃ and G₄ are preferably C₁-C₄alkyl, in particular methyl.

[0044] One of the preferred meanings of R is propyl.

[0045] One of the preferred meanings of R* is C₁-C₄alkyl, in particularmethyl.

[0046] One of the preferred meanings of R₁ is C₁-C₈alkyl such as methylor 3-heptyl.

[0047] An example of hydroxyalkyl containing not more than 18 carbonatoms is 2-hydroxyethyl or hydroxybutyl.

[0048] Examples of C₂-C₁₈alkyl interrupted by oxygen or sulphur, e.g.one or more oxygen or sulphur, are 2-methoxyethyl, 2-ethoxyethyl,3-methoxypropyl, 3-ethoxypropyl, 3-butoxypropyl, 3-octyloxypropyl,4-methoxybutyl, 2-methylthioethyl, 2-ethylthioethyl, 3-methylthiopropyl,3-ethylthiopropyl, 3-butylthiopropyl, 3-octylthiopropyl or4-methylthiobutyl.

[0049] Examples of C₂-C₁₈alkyl interrupted by >N—R₀, e.g. one or more>N—R₀, are —CH₂CH₂—N(R₀)—CH₃, —CH₂CH₂—N(R₀)—CH₂CH₃, —CH₂CH₂CH₂—N(R₀)—CH₃or —CH₂CH₂CH₂—N(R₀)—CH₂CH₃.

[0050] Examples of alkenyl containing not more than 18 carbon atoms areallyl, 2-methylallyl, butenyl, hexenyl, undecenyl and octadecenyl.Alkenyls in which the carbon atom in the 1-position is saturated are ofinterest, and allyl is of particular interest. Thus, one of thepreferred meanings of R is allyl. The alkenyl groups contain only onedouble bond.

[0051] An example of alkynyl containing not more than 18 carbon atoms is2-butynyl.

[0052] Examples of alkoxy containing not more than 18 carbon atoms aremethoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, pentoxy,isopentoxy, hexoxy, heptoxy, octoxy, decyloxy, dodecyloxy,tetradecyloxy, hexadecyloxy and octadecyloxy. C₁-C₁₂Alkoxy, inparticular methoxy, propoxy, butoxy and octyloxy, is one of thepreferred meanings of R.

[0053] Examples of acyl containing not more than 8 carbon atoms areformyl, acetyl, propionyl, butyryl, pentanoyl, hexanoyl, heptanoyl,octanoyl, acryloyl, methacryloyl and benzoyl. C₁-C₈Alkanoyl,C₃-C₈alkenyl and benzoyl are preferred. Acetyl and acryloyl areespecially preferred.

[0054] Examples of C₁-C₁₈alkanoyl are formyl, acetyl, propionyl,butyryl, pentanoyl, hexanoyl, heptanoyl and octanoyl.

[0055] Examples of C₁-C₁₈alkanoyloxy are formyloxy, acetyloxy,propionyloxy, butyryloxy, pentanoyloxy, hexanoyloxy, heptanoyloxy andoctanoyloxy.

[0056] Examples of (C₁-C₁₈alkoxy)carbonyl are methoxycarbonyl,ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, pentyloxycarbonyl,hexyloxycarbonyl, heptyloxycarbonyl and octyloxycarbonyl.

[0057] Examples of C₅-C₁₂cycloalkyl which is unsubstituted orsubstituted by —OH, C₁-C₄alkyl and/or C₁-C₄alkoxy, e.g. 1, 2 or 3-OH,C₁-C₄alkyl and/or C₁-C₄alkoxy, are cyclopentyl, methylcyclopentyl,dimethylcyclopentyl, cyclohexyl, methylcyclohexyl, dimethylcyclohexyl,trimethylcyclohexyl, t-butylcyclohexyl, cyclooctyl, cyclodecyl,cyclododecyl and methoxycyclohexyl. Unsubstituted or substitutedC₅-C₈cycloalkyl, in particular cyclohexyl, is preferred.

[0058] Examples of C₅-C₁₂cycloalkoxy are cyclopentoxy, cyclohexoxy,cycloheptoxy, cyclooctoxy, cyclodecyloxy, cyclododecyloxy andmethylcyclohexoxy. C₅-C₈Cycloalkoxy, in particular cyclopentoxy andcyclohexoxy, is preferred.

[0059] Examples of phenyl substituted by C₁-C₄alkyl and/or C₁-C₄alkoxy,e.g. 1, 2 or 3 C₁-C₄alkyl and/or C₁-C₄alkoxy, are methylphenyl,dimethylphenyl, trimethylphenyl, t-butylphenyl, di-t-butylphenyl,3,5-di-t-butyl-4-methylphenyl, methoxyphenyl, ethoxyphenyl andbutoxyphenyl.

[0060] Examples of C₇-C₁₂phenylalkyl which is unsubstituted orsubstituted on the phenyl radical by —OH, C₁-C₄alkyl and/or C₁-C₄alkoxy,e.g. 1, 2 or 3 —OH, C₁-C₄alkyl and/or C₁-C₄alkoxy, are benzyl,methylbenzyl, dimethylbenzyl, trimethylbenzyl, t-butylbenzyl,2-phenylethyl and methoxybenzyl. C₇-C₉phenylalkyl, in particular benzyl,is preferred.

[0061] Examples of C₇-C₁₂phenylalkoxy unsubstituted or substituted onthe phenyl radical by C₁-C₄alkyl and/or C₁-C₄alkoxy, e.g. 1, 2 or 3C₁-C₄alkyl and/or C₁-C₄alkoxy, are benzyloxy, methylbenzyloxy,dimethylbenzyloxy, trimethylbenzyloxy, t-butylbenzyloxy, 2-phenylethoxyand methoxybenzyloxy.

[0062] C₇-C₉phenylalkoxy, in particular benzyloxy, is preferred.

[0063] An example of C₁-C₁₈hydroxyalkoxy is hydroxybutoxy.

[0064] An example of C₂-C₁₈alkenyloxy is 2-propenyloxy.

[0065] Examples of alkylene containing not more than 12 carbon atoms aremethylene, ethylene, propylene, trimethylene, tetramethylene,pentamethylene, hexamethylene, octamethylene, decamethylene anddodecamethylene. One of the preferred meanings of X is C₂-C₁₂alkylene orC₄-C₁₂alkylene, in particular C₂-C₆alkylene or C₄-C₆alkylene.

[0066] Examples of alkylene containing not more than 16 carbon atoms andinterrupted by —O— or —S—, e.g. one or more —O— or —S—, are3-oxapentane-1,5-diyl, 4-oxaheptane-1,7-diyl, 3,6-dioxaoctane-1,8-diyl,4,7-dioxadecane-1,10-diyl, 4,9-dioxadodecane-1,12-diyl,3,6,9-trioxaundecane-1,11-diyl, 4,7,10-trioxatridecane-1,13-diyl,3-thiapentane-1,5-diyl, 4-thiaheptane-1,7-diyl,3,6-dithiaoctane-1,8-diyl, 4,7-dithiadecane-1,10-diyl,4,9-dithiadodecane-1,12-diyl, 3,6,9-trithiaundecane-1,11-diyl and4,7,10-trithiatridecane-1,13-diyl.

[0067] Examples of alkylene containing not more than 16 carbon atoms andinterrupted by >N—R₀′, e.g. one or more >N—R₀′, are—CH₂CH₂—N(R₀)—CH₂CH₂—, —CH₂CH₂CH₂—N(R₀)—CH₂CH₂CH₂— and—CH₂CH₂—CH(CH₃)—N(R₀)—CH₂CH₂CH₂CH₂CH₂CH₂—N(R₀)—CH(CH₃)—CH₂CH₂—.

[0068] One of the preferred meanings of X is—CH₂CH₂—CH(CH₃)—N(R₀)—(CH₂)₂₋₆—N(R₀)—CH(CH₃)—CH₂CH₂—.

[0069] An example of C₂-C₁₂alkenylene is —CH₂CH═CHCH₂—. C₄-C₁₂alkenyleneis preferred.

[0070] An example of C₂-C₁₂alkynylene is —CH₂CH₂—C≡C—CH₂CH₂—.C₆-C₁₂alkynylene is preferred.

[0071] An example of C₅-C₁₂cycloalkylene is cyclohexylene.

[0072] An example of C₁-C₄alkylene-(C₅-C₁₂cycloalkylene)-C₁-C₄alkyleneis cyclohexylenedimethylene.

[0073] Examples ofC₅-C₁₂cycloalkylene-(C₁-C₄alkylene)-C₅-C₁₂cycloalkylene aremethylenedicyclohexylene and isopropylidenedicyclohexylene.

[0074] An example of phenylene-(C₁-C₄alkylene)-phenylene ismethylenediphenylene.

[0075] An example of C₁-C₄alkylene-phenylene-C₁-C₄alkylene isphenylenedimethylene.

[0076] C₅-C₂₅alkantriyl may be for example a group H₃C—C(CH₂)₃—.

[0077] C₄-C₁₈triacyl may be for example an aliphatic C₄-C₁₈triacyl, analiphatic C₆-C₁₈triacyl substituted by nitrogen, a cycloaliphaticC₆-C₁₈triacyl, an aromatic C₉-C₁₈triacyl or a heterocyclicC₉-C₁₈triacyl.

[0078] An aliphatic C₄-C₁₈triacyl is e.g. C₄-C₁₈alkanetrioylunsubstituted or substituted by OH. Preferred examples are thosetriacyls derived from methanetricarboxylic acid,1,1,2-ethanetricarboxylic acid, 1,2,3-propanetricarboxylic acid, citricacid or 1,2,3-butanetricarboxylic acid.

[0079] An aliphatic C₆-C₁₈triacyl substituted by nitrogen is e.g.

[0080] The group N(CH₂CO—)₃ is especially preferred.

[0081] A cycloaliphatic C₆-C₁₈triacyl is e.g.

[0082] An aromatic C₉-C₁₈triacyl is e.g. a triacyl derived from1,2,4-benzenetricarboxylic acid or 1,3,5-benzenetricarboxylic acid.

[0083] A heterocyclic C₉-C₁₈triacyl is e.g. a group of the formula

[0084] C₅-C₂₀alkantetrayl may be for example C(CH₂)₄—.

[0085] A C₆-C₂₂tetraacyl is for example an aliphatic C₆-C₁₈tetraacyl, analiphatic C₁₀-C₁₈tetraacyl substituted by nitrogen, a cycloaliphaticC₁₀-C₂₂tetraacyl or an aromatic C₁₀-C₁₈tetraacyl.

[0086] An aliphatic C₆-C₁₈tetraacyl is e.g. C₆-C₁₈alkanetetraoyl.Preferred examples are those tetraacyls derived from1,1,3,3-propanetetracarboxylic acid or 1,2,3,4-butanetetracarboxylicacid.

[0087] An aliphatic C₁₀-C₁₈tetraacyl substituted by nitrogen is e.g. agroup of the formula

[0088] A tetraacyl derived from ethylenediaminetetraacetic acid ispreferred.

[0089] A cycloaliphatic C₁₀-C₂₂tetraacyl is e.g. acycloalkanetetracarbonyl or a cycloalkenetetracarbonyl such as

[0090] An aromatic C₁₀-C₁₈tetraacyl is for example a tetraacyl derivedfrom 1,2,4,5-benzenetetracarboxylic acid.

[0091] R is preferably C₁-C₁₂alkyl, C₁-C₁₂hydroxyalkyl, C₂-C₈alkenyl orC₅-C₈cycloalkyl; or for example propyl, C₁-C₁₂hydroxyalkyl, C₂-C₈alkenylor C₅-C₈cycloalkyl; in particular methyl, propyl, butyl, octyl,hydroxybutyl, 2-propenyl or cyclohexyl.

[0092] R* is preferably hydrogen, C₁-C₄alkyl, oxyl, —OH, C₃-C₆alkenyl,benzyl, C₁-C₈acyl, C₁-C₁₂alkoxy, C₁-C₁₂hydroxyalkoxy, C₂-C₈alkenyloxy orC₅-C₈cycloalkoxy, in particular hydrogen, methyl, allyl, acetyl,methoxy, propoxy, butoxy, octyloxy, hydroxybutoxy, 2-propenyloxy orcyclohexyloxy.

[0093] n is preferably 2, 3 or 4, in particular 2.

[0094] A preferred embodiment of the present invention relates to acompound of the formula (IA) wherein,

[0095] when n is 1, X is C₂-C₁₂alkyl, C₂-C₁₂hydroxyalkyl, C₂-C₁₂alkylinterrupted by oxygen or >N—R₀ with R₀ being as defined below;C₂-C₁₈alkenyl, C₅-C₈cycloalkyl unsubstituted or substituted byC₁-C₄alkyl; or benzyl unsubstituted or substituted on the phenyl radicalby —OH and/or C₁-C₄alkyl; or X is one of the groups of the formulae(II-a) to (II-m);

[0096] Y₁, Y₂, Y₅, Y₆, Y₇ and Y₉ are a direct bond, C₁-C₆alkylene,cyclohexylene or phenylene;

[0097] Y₃, Y₄, Y₈, Y₁₀, Y₁₁ and Y₁₂ are C₂-C₆alkylene, cyclohexylene orphenylene;

[0098] R₁, R₂, R₃, R₄, R₅, R₆, R₇ and R₁₃ are hydrogen, C₁-C₁₂alkyl,C₂-C₁₂alkyl interrupted by oxygen or >N—R₀ with R₀ being as definedbelow; C₂-C₁₈alkenyl, C₅-C₈cycloalkyl unsubstituted or substituted byC₁-C₄alkyl; phenyl unsubstituted or substituted by C₁-C₄alkyl; or benzylunsubstituted or substituted on the phenyl radical by C₁-C₄alkyl;

[0099] Z₁, Z₂ and Z₃ are independently of one another —O— or >N—R₁₆;

[0100] R₀, R₈, R₉, R₁₀, R₁₁, R₁₂, R₁₄, R₁₅ and R₁₆ are independently ofone another hydrogen, C₁-C₁₂alkyl, C₃-C₁₈alkenyl, C₅-C₈cycloalkyl whichis unsubstituted or substituted by C₁-C₄alkyl; or benzyl unsubstitutedor substituted on the phenyl radical by C₁-C₄alkyl; with the provisothat the formula (II-b) is different from ethoxycarbonyl;

[0101] when n is 2, X is C₂-C₆alkylene, C₂-C₁₆alkylene interrupted byoxygen or >N—R₀′ with R₀′ being as defined below; C₂-C₆alkenylene,cyclohexylene, cyclohexylene-(C₁-C₄alkylene)-cyclohexylene,C₁-C₄alkylene-cyclohexylene-C₁-C₄alkylene orC₁-C₄alkylene-phenylene-C₁-C₄alkylene, or X is one of the groups of theformulae (III-a) to (III-j);

[0102] Y₁′, Y₁″, Y₂′, Y₂″, Y₅′, Y₅″, Y₆′, Y₆″, Y₇′ and Y₇″ areindependently of one another a direct bond, C₁-C₆alkylene, cyclohexyleneor phenylene;

[0103] Y₃′, Y₃″, Y₄′, Y₄″, Y₈′, Y₈″, Y₁₁′, Y₁₁″, Y₁₂′ and Y₁₂″ areindependently of one another C₂-C₆alkylene, cyclohexylene or phenylene;

[0104] A₁, A₂, A₃, A₄, A₅, A₆, A₇, A₈ and A₉ are C₂-C₆alkylene,C₂-C₆alkylene interrupted by oxygen or >N—R₀′ with R₀′ being as definedbelow, C₂-C₆alkenylene, cyclohexylene,cyclohexylene-(C₁-C₄alkylene)-cyclohexylene,C₁-C₄alkylene-cyclohexylene-C₁-C₄alkylene orC₁-C₄alkylene-phenylene-C₁-C₄alkylene; and A₁ and A₅ are additionally adirect bond;

[0105] Z₁′, Z₂′ and Z₃′ are independently of one another —O— or >N—R₆′;and

[0106] R₀′, R₁₄′ and R₁₆′ are independently of one another hydrogen,C₁-C₁₂alkyl, C₃-C₁₈alkenyl, C₅-C₈cycloalkyl which is unsubstituted orsubstituted by C₁-C₄alkyl; or benzyl which is unsubstituted orsubstituted on the phenyl radical by C₁-C₄alkyl;

[0107] when n is 3, X is C₅-C₁₀alkantriyl, an aliphatic C₄-C₁₈triacyl,an aliphatic C₆-C₁₈triacyl substituted by nitrogen; a cycloaliphaticC₆-C₁₈triacyl, an aromatic C₉-C₁₈triacyl, a heterocyclic C₉-C₁₈triacylor a group of the formula (IV);

[0108] Y₁₃′, Y₁₃″ and Y₁₃′″ are independently of one anotherC₂-C₆alkylene, cyclohexylene or phenylene;

[0109] Z₁″, Z₂″ and Z₃″ are independently of one another —O— or >N—R₁₆″;and

[0110] R₁₆″ is hydrogen, C₁-C₁₂alkyl, C₃-C₁₈alkenyl, C₅-C₈cycloalkylwhich is unsubstituted or substituted by C₁-C₄alkyl; or benzyl which isunsubstituted or substituted on the phenyl radical by C₁-C₄alkyl; and

[0111] when n is 4, X is C₅-C₁₀alkantetrayl, an aliphaticC₆-C₁₈tetraacyl, an aliphatic C₁₀-C₁₈tetraacyl substituted by nitrogen,a cycloaliphatic C₁₀-C₂₂tetraacyl, an aromatic C₁₀-C₁₈tetraacyl or agroup of the formula (V);

[0112] Y₁₄′ and Y₁₄″ are independently of one another C₂-C₆alkylene,cyclohexylene or phenylene;

[0113] Z₁′″, Z₂′″, M and T are independently of one another —O— or>N—R₁₆′″, and M and T are additionally —S—;

[0114] R₁₆′″ is hydrogen, C₁-C₁₂alkyl, C₃-C₁₈alkenyl, C₅-C₈cycloalkylwhich is unsubstituted or substituted by C₁-C₄alkyl; or benzyl which isunsubstituted or substituted on the phenyl radical by C₁-C₄alkyl; and

[0115] q is an integer from 2 to 12.

[0116] A further preferred embodiment of the present invention relatesto a compound of the formula (IA) wherein,

[0117] when n is 1, X is C₂-C₆alkyl, C₂-C₆hydroxyalkyl, C₂-C₆alkylinterrupted by oxygen; allyl, cyclohexyl, benzyl or one of the groups ofthe formulae (II-a) to (II-l);

[0118] Y₁, Y₂, Y₅, Y₆, Y₇ and Y₉ are a direct bond, C₁-C₆alkylene,cyclohexylene or phenylene;

[0119] Y₃, Y₄, Y₈, Y₁₀, Y₁, and Y₁₂ are C₂-C₆alkylene, cyclohexylene orphenylene;

[0120] R₁, R₂, R₃, R₄, R₅, R₆, R₇ and R₁₃ are hydrogen, C₁-C₈alkyl,C₂-C₆alkyl interrupted by oxygen;

[0121] allyl, cyclohexyl, phenyl or benzyl;

[0122] Z₁, Z₂ and Z₃ are independently of one another —O— or >N—R₁₆;

[0123] R₀, R₈, R₉, R₁₀, R₁₁, R₁₂, R₁₄, R₁₅ and R₁₆ are independently ofone another hydrogen, C₁-C₆alkyl, allyl, cyclohexyl or benzyl;

[0124] with the proviso that the formula (II-b) is different fromethoxycarbonyl;

[0125] when n is 2, X is C₂-C₆alkylene, C₂-C₁₄alkylene interrupted byoxygen or >N—R₀′;

[0126] cyclohexylene or one of the groups of the formulae (III-a) to(III-j);

[0127] Y₁′, Y₁″, Y₂′, Y₂″, Y₅′, Y₅″, Y₆′, Y₆″, Y₇′ and Y₇″ areindependently of one another a direct bond, C₁-C₆alkylene, cyclohexyleneor phenylene;

[0128] Y₃′, Y₃″, Y₄′, Y₄″, Y₈′, Y₈″, Y₁₁′, Y₁₁″, Y₁₂′ and Y₁₂″ areindependently of one another C₂-C₆alkylene, cyclohexylene or phenylene;

[0129] A₁, A₂, A₃, A₄, A₅, A₆, A₇, A₈ and A₉ are C₂-C₆alkylene,C₂-C₆alkylene interrupted by oxygen;

[0130] cyclohexylene or phenylene; and A₁ and A₅ are additionally adirect bond;

[0131] Z₁′, Z₂′ and Z₃′ are independently of one another —O— or >N—R₁₆′;and

[0132] R₀′, R₁₄′ and R₁₆′ are independently of one another hydrogen,C₁-C₆alkyl, allyl, cyclohexyl or benzyl:

[0133] when n is 3, X is a group of the formula (IV);

[0134] Y₁₃′, Y₁₃″ and Y₁₃′″ are independently of one anotherC₂-C₆alkylene, cyclohexylene or phenylene;

[0135] Z₁″, Z₂″ and Z₃″ are independently of one another —O— or >N—R₁₆″;and

[0136] R₁₆″ is hydrogen, C₁-C₆alkyl, allyl, cyclohexyl or benzyl; and

[0137] when n is 4, X is a group of the formula (V);

[0138] Y₁₄′ and Y₁₄″ are independently of one another C₂-C₆alkylene,cyclohexylene or phenylene;

[0139] Z₁′″, Z₂′″, M and T are independently of one another —O— or>N—R₁₆′″;

[0140] R₁₆′″ is hydrogen, C₁-C₆alkyl, allyl, cyclohexyl or benzyl; and qis an integer from 2 to 12.

[0141] When n is 2, X is preferably C₂-C₆alkylene or C₂-C₁₄alkyleneinterrupted by oxygen or >N—R₀′; or X is a group of the formula (III-a),(III-b) or (III-j).

[0142] Also preferred is a compound of the formula (IA) wherein

[0143] G₁, G₂, G₃ and G₄ are methyl;

[0144] R is C₁-C₁₂alkyl, C₁-C₁₂hydroxyalkyl, C₂-C₈alkenyl orC₅-C₈cycloalkyl;

[0145] when n is 1, X is a group of the formula (II-a) or (II-l);

[0146] Y₁ is a direct bond or C₁-C₆alkylene;

[0147] R₁ is C₁-C₈alkyl;

[0148] Z₁, Z₂ and Z₃ are >N—R₁₆;

[0149] R₁₄, R₁₅ and R₁₆ are independently of one another hydrogen orC₁-C₆alkyl; and

[0150] Y₁₂ is C₂-C₆alkylene;

[0151] when n is 2, X is C₂-C₆alkylene, C₂-C₁₄alkylene interrupted by2>N—H; or a group of the formula (III-b) or (III-j);

[0152] Y₂′, Y₂″, Y₁₂′ and Y₁₂″ are independently of one anotherC₁-C₆alkylene;

[0153] A₂ is C₂-C₆alkylene;

[0154] Z₁′, Z₂′ and Z₃′ are independently of one another >N—R₁₆′; and

[0155] R₁₄′ and R₁₆′ are independently of one another hydrogen orC₁-C₆alkyl;

[0156] when n is 3, X is-a group of the formula (IV);

[0157] Y₁₃′, Y₁₃″ and Y₁₃′″ are independently of one anotherC₂-C₆alkylene;

[0158] Z₁″, Z₂″ and Z₃″ are a group >N—H; and

[0159] when n is 4, X is a group of the formula (V);

[0160] Y₁₄′ and Y₁₄″ are independently of one another C₂-C₆alkylene;

[0161] Z₁′″, Z₂′″, M and T are a group >N—H; and

[0162] q is an integer from 2 to 6.

[0163] A compound of the formula (IA) which is of interest is onewherein

[0164] G₁, G₂, G₃ and G₄ are methyl;

[0165] R is propyl or 2-propenyl;

[0166] n is 2;

[0167] X is C₂-C₆alkylene or a group of the formula (III-b);

[0168] Y₂′ and Y₂″ are independently of one another C₁-C₆alkylene; and

[0169] A₂ is C₂-C₆alkylene.

[0170] Examples of compounds of the formula (IA) are:

[0171] Particularly preferred examples of the compounds of the formula(IA) are:

[0172] Another preferred embodiment of the present invention relates toa compound of the formula (IB) wherein

[0173] G₁, G₂, G₃ and G₄ are methyl;

[0174] R* is hydrogen, C₁-C₄alkyl, C₁-C₈alkoxy, C₃-C₈alkenyloxy orC₅-C₈cycloalkoxy;

[0175] n* is 1 or 2;

[0176] Z₁* and Z₂* are —O— or >N—R₃*; and

[0177] R₁*, R₂* and R₃* are independently of one another hydrogen,C₁-C₆alkyl, allyl, cyclohexyl or benzyl.

[0178] A further preferred embodiment of the present invention relatesto a compound of the formula (IB) wherein

[0179] G₁, G₂, G₃ and G₄ are methyl;

[0180] R* is hydrogen or C₁-C₄alkyl;

[0181] n* is 1 or 2;

[0182] Z₁* and Z₂* are —O—; and

[0183] R₁* and R₂* are independently of one another C₁-C₆alkyl.

[0184] Examples of compounds of the formula (IB) are

[0185] The compounds of the formulae (IA) and (IB) can be prepared, forexample, according to the following reaction scheme.

[0186] wherein G₁, G₂, G₃, G₄, X and X* as well as n and n* are asdefined above and Hal means e.g. Br, Cl or J, preferably Cl or Br.

[0187] The reaction can be carried out without the isolation of theionic intermediate. Suitable organic solvents are common aprotic organicsolvents, for example toluene, xylene, mesitylene or tetrahydrofuran, inparticular toluene. The ratio of the reactants is preferablystoichiometric but it is also possible to use the imidazolidinone in anexcess of up to 40 mol %. Examples of suitable bases are potassiumtert-butoxide, potassium hydroxide and sodium hydroxide. A preferredbase is potassium tert-butoxide. The base can be applied in an excess ofup to 20 mol %. The reaction temperature is for example from roomtemperature to 80° C., preferably 30-40° C.

[0188] The substitution of the nitrogen >N—H of the final product (thatmeans the introduction of the radical R* different from hydrogen or theintroduction of the radical —OR) can be carried out according to knownprocesses.

[0189] The imidazolidinone starting material is known and can beprepared in analogy to known processes. When G₁, G₂, G₃ and G₄ aremethyl, it can also be prepared as shown in SCHEME 2 below.

[0190] These reactions are described in EXAMPLE 1, steps 1.1 and 1.2.

[0191] The preparation of the compounds according to the presentinvention is shown in more detail in the working examples.

[0192] The compounds of this invention are very effective in improvingthe light, heat and oxidation resistance of organic materials.

[0193] Examples of such organic materials are:

[0194] 1. Polymers of monoolefins and diolefins, for examplepolypropylene, polyisobutylene, polybut-1-ene, poly-4-methylpent-1-ene,polyvinylcyclohexane, polyisoprene or polybutadiene, as well as polymersof cycloolefins, for instance of cyclopentene or norbornene,polyethylene (which optionally can be crosslinked), for example highdensity polyethylene (HDPE), high density and high molecular weightpolyethylene (HDPE-HMW), high density and ultrahigh molecular weightpolyethylene (HDPE-UHMW), medium density polyethylene (MDPE), lowdensity polyethylene (LDPE), linear low density polyethylene (LLDPE),(VLDPE) and (ULDPE).

[0195] Polyolefins, i.e. the polymers of monoolefins exemplified in thepreceding paragraph, preferably polyethylene and polypropylene, can beprepared by different, and especially by the following, methods:

[0196] a) radical polymerisation (normally under high pressure and atelevated temperature).

[0197] b) catalytic polymerisation using a catalyst that normallycontains one or more than one metal of groups IVb, Vb, VIb or VIII ofthe Periodic Table. These metals usually have one or more than oneligand, typically oxides, halides, alcoholates, esters, ethers, amines,alkyls, alkenyls and/or aryls that may be either π- or σ-coordinated.These metal complexes may be in the free form or fixed on substrates,typically on activated magnesium chloride, titanium(III) chloride,alumina or silicon oxide. These catalysts may be soluble or insoluble inthe polymerisation medium. The catalysts can be used by themselves inthe polymerisation or further activators may be used, typically metalalkyls, metal hydrides, metal alkyl halides, metal alkyl oxides or metalalkyloxanes, said metals being elements of groups Ia, IIa and/or IIIa ofthe Periodic Table. The activators may be modified conveniently withfurther ester, ether, amine or silyl ether groups. These catalystsystems are usually termed Phillips, Standard Oil Indiana, Ziegler(-Natta), TNZ (DuPont), metallocene or single site catalysts (SSC).

[0198] 2. Mixtures of the polymers mentioned under 1), for examplemixtures of polypropylene with polyisobutylene, polypropylene withpolyethylene (for example PP/HDPE, PP/LDPE) and mixtures of differenttypes of polyethylene (for example LDPE/HDPE).

[0199] 3. Copolymers of monoolefins and diolefins with each other orwith other vinyl monomers, for example ethylene/propylene copolymers,linear low density polyethylene (LLDPE) and mixtures thereof with lowdensity polyethylene (LDPE), propylene/but-1-ene copolymers,propylene/isobutylene copolymers, ethylene/but-1-ene copolymers,ethylene/hexene copolymers, ethylene/methylpentene copolymers,ethylene/heptene copolymers, ethylene/octene copolymers,ethylene/vinylcyclohexane copolymers, ethylene/cycloolefin copolymers(e.g. ethylene/norbornene like COC), ethylene/1-olefins copolymers,where the 1-olefin is gene-rated in-situ; propylene/butadienecopolymers, isobutylene/isoprene copolymers, ethylene/vinylcyclohexenecopolymers, ethylene/alkyl acrylate copolymers, ethylene/alkylmethacrylate copolymers, ethylene/vinyl acetate copolymers orethylene/acrylic acid copolymers and their salts (ionomers) as well asterpolymers of ethylene with propylene and a diene such as hexadiene,dicyclopentadiene or ethylidene-norbornene; and mixtures of suchcopolymers with one another and with polymers mentioned in 1) above, forexample polypropylene/ethylene-propylene copolymers, LDPE/ethylene-vinylacetate copolymers (EVA), LDPE/ethylene-acrylic acid copolymers (EAA),LLDPE/EVA, LLDPE/EAA and alternating or random polyalkylene/carbonmonoxide copolymers and mixtures thereof with other polymers, forexample polyamides.

[0200] 4. Hydrocarbon resins (for example C₅-C₉) including hydrogenatedmodifications thereof (e.g. tackifiers) and mixtures of polyalkylenesand starch.

[0201] Homopolymers and copolymers from 1.)-4.) may have anystereostructure including syndiotactic, isotactic, hemi-isotactic oratactic; where atactic polymers are preferred. Stereoblock polymers arealso included.

[0202] 5. Polystyrene, poly(p-methylstyrene), poly(α-methylstyrene).

[0203] 6. Aromatic homopolymers and copolymers derived from vinylaromatic monomers including styrene, α-methylstyrene, all isomers ofvinyl toluene, especially p-vinyltoluene, all isomers of ethyl styrene,propyl styrene, vinyl biphenyl, vinyl naphthalene, and vinyl anthracene,and mixtures thereof. Homopolymers and copolymers may have anystereostructure including syndiotactic, isotactic, hemi-isotactic oratactic; where atactic polymers are preferred. Stereoblock polymers arealso included.

[0204] 6a. Copolymers including aforementioned vinyl aromatic monomersand comonomers selected from ethylene, propylene, dienes, nitriles,acids, maleic anhydrides, maleimides, vinyl acetate and vinyl chlorideor acrylic derivatives and mixtures thereof, for examplestyrene/butadiene, styrene/acrylonitrile, styrene/ethylene(interpolymers), styrene/alkyl methacrylate, styrene/butadiene/alkylacrylate, styrene/butadiene/alkyl methacrylate, styrene/maleicanhydride, styrene/acrylonitrile/methyl acrylate; mixtures of highimpact strength of styrene copolymers and another polymer, for example apolyacrylate, a diene polymer or an ethylene/propylene/diene terpolymer;and block copolymers of styrene such as styrene/butadiene/styrene,styrene/isoprene/styrene, styrene/ethylene/butylene/styrene orstyrene/ethylene/propylene/styrene.

[0205] 6b. Hydrogenated aromatic polymers derived from hydrogenation ofpolymers mentioned under 6.), especially includingpolycyclohexylethylene (PCHE) prepared by hydrogenating atacticpolystyrene, often referred to as polyvinylcyclohexane (PVCH).

[0206] 6c. Hydrogenated aromatic polymers derived from hydrogenation ofpolymers mentioned under 6a.).

[0207] Homopolymers and copolymers may have any stereostructureincluding syndiotactic, isotactic, hemi-isotactic or atactic; whereatactic polymers are preferred. Stereoblock polymers are also included.

[0208] 7. Graft copolymers of vinyl aromatic monomers such as styrene orα-methylstyrene, for example styrene on polybutadiene, styrene onpolybutadiene-styrene or polybutadiene-acrylonitrile copolymers; styreneand acrylonitrile (or methacrylonitrile) on polybutadiene; styrene,acrylonitrile and methyl methacrylate on polybutadiene; styrene andmaleic anhydride on polybutadiene; styrene, acrylonitrile and maleicanhydride or maleimide on polybutadiene; styrene and maleimide onpolybutadiene; styrene and alkyl acrylates or methacrylates onpolybutadiene; styrene and acrylonitrile on ethylene/propylene/dieneterpolymers; styrene and acrylonitrile on polyalkyl acrylates orpolyalkyl methacrylates, styrene and acrylonitrile on acrylate/butadienecopolymers, as well as mixtures thereof with the copolymers listed under6), for example the copolymer mixtures known as ABS, MBS, ASA or AESpolymers.

[0209] 8. Halogen-containing polymers such as polychloroprene,chlorinated rubbers, chlorinated and brominated copolymer ofisobutylene-isoprene (halobutyl rubber), chlorinated or sulfochlorinatedpolyethylene, copolymers of ethylene and chlorinated ethylene,epichlorohydrin homo- and copolymers, especially polymers ofhalogen-containing vinyl compounds, for example polyvinyl chloride,polyvinylidene chloride, polyvinyl fluoride, polyvinylidene fluoride, aswell as copolymers thereof such as vinyl chloride/vinylidene chloride,vinyl chloride/vinyl acetate or vinylidene chloride/vinyl acetatecopolymers.

[0210] 9. Polymers derived from α,β-unsaturated acids and derivativesthereof such as polyacrylates and polymethacrylates; polymethylmethacrylates, polyacrylamides and polyacrylonitriles, impact-modifiedwith butyl acrylate.

[0211] 10. Copolymers of the monomers mentioned under 9) with each otheror with other unsaturated monomers, for example acrylonitrile/butadienecopolymers, acrylonitrile/alkyl acrylate copolymers,acrylonitrile/alkoxyalkyl acrylate or acrylonitrile/vinyl halidecopolymers or acrylonitrile/alkyl methacrylate/butadiene terpolymers.

[0212] 11. Polymers derived from unsaturated alcohols and amines or theacyl derivatives or acetals thereof, for example polyvinyl alcohol,polyvinyl acetate, polyvinyl stearate, polyvinyl benzoate, polyvinylmaleate, polyvinyl butyral, polyallyl phthalate or polyallyl melamine;as well as their copolymers with olefins mentioned in 1) above.

[0213] 12. Homopolymers and copolymers of cyclic ethers such aspolyalkylene glycols, polyethylene oxide, polypropylene oxide orcopolymers thereof with bisglycidyl ethers.

[0214] 13. Polyacetals such as polyoxymethylene and thosepolyoxymethylenes which contain ethylene oxide as a comonomer;polyacetals modified with thermoplastic polyurethanes, acrylates or MBS.

[0215] 14. Polyphenylene oxides and sulfides, and mixtures ofpolyphenylene oxides with styrene polymers or polyamides.

[0216] 15. Polyurethanes derived from hydroxyl-terminated polyethers,polyesters or polybutadienes on the one hand and aliphatic or aromaticpolyisocyanates on the other, as well as precursors thereof.

[0217] 16. Polyamides and copolyamides derived from diamines anddicarboxylic acids and/or from aminocarboxylic acids or thecorresponding lactams, for example polyamide 4, polyamide 6, polyamide6/6, 6/10, 6/9, 6/12, 4/6, 12/12, polyamide 11, polyamide 12, aromaticpolyamides starting from m-xylene diamine and adipic acid; polyamidesprepared from hexamethylenediamine and isophthalic or/and terephthalicacid and with or without an elastomer as modifier, for examplepoly-2,4,4,-trimethylhexamethylene terephthalamide or poly-m-phenyleneisophthalamide; and also block copolymers of the aforementionedpolyamides with polyolefins, olefin copolymers, ionomers or chemicallybonded or grafted elastomers; or with polyethers, e.g. with polyethyleneglycol, polypropylene glycol or polytetramethylene glycol; as well aspolyamides or copolyamides modified with EPDM or ABS; and polyamidescondensed during processing (RIM polyamide systems).

[0218] 17. Polyureas, polyimides, polyamide-imides, polyetherimids,polyesterimids, polyhydantoins and polybenzimidazoles.

[0219] 18. Polyesters derived from dicarboxylic acids and diols and/orfrom hydroxycarboxylic acids or the corresponding lactones, for examplepolyethylene terephthalate, polybutylene terephthalate,poly-1,4-dimethylolcyclohexane terephthalate, polyalkylene naphthalate(PAN) and polyhydroxybenzoates, as well as block copolyether estersderived from hydroxyl-terminated polyethers; and also polyestersmodified with polycarbonates or MBS.

[0220] 19. Polycarbonates and polyester carbonates.

[0221] 20. Polyketones.

[0222] 21. Polysulfones, polyether sulfones and polyether ketones.

[0223] 22. Crosslinked polymers derived from aldehydes on the one handand phenols, ureas and melamines on the other hand, such asphenol/formaldehyde resins, urea/formaldehyde resins andmelamine/formaldehyde resins.

[0224] 23. Drying and non-drying alkyd resins.

[0225] 24. Unsaturated polyester resins derived from copolyesters ofsaturated and unsaturated dicarboxylic acids with polyhydric alcoholsand vinyl compounds as crosslinking agents, and also halogen-containingmodifications thereof of low flammability.

[0226] 25. Crosslinkable acrylic resins derived from substitutedacrylates, for example epoxy acrylates, urethane acrylates or polyesteracrylates.

[0227] 26. Alkyd resins, polyester resins and acrylate resinscrosslinked with melamine resins, urea resins, isocyanates,isocyanurates, polyisocyanates or epoxy resins.

[0228] 27. Crosslinked epoxy resins derived from aliphatic,cycloaliphatic, heterocyclic or aromatic glycidyl compounds, e.g.products of diglycidyl ethers of bisphenol A and bisphenol F, which arecrosslinked with customary hardeners such as anhydrides or amines, withor without accelerators.

[0229] 28. Natural polymers such as cellulose, rubber, gelatin andchemically modified homologous derivatives thereof, for examplecellulose acetates, cellulose propionates and cellulose butyrates, orthe cellulose ethers such as methyl cellulose; as well as rosins andtheir derivatives.

[0230] 29. Blends of the aforementioned polymers (polyblends), forexample PP/EPDM, Poly-amide/EPDM or ABS, PVC/EVA, PVC/ABS, PVC/MBS,PC/ABS, PBTP/ABS, PC/ASA, PC/PBT, PVC/CPE, PVC/acrylates,POM/thermoplastic PUR, PC/thermoplastic PUR, POM/acrylate, POM/MBS,PPO/HIPS, PPO/PA 6.6 and copolymers, PA/HDPE, PA/PP, PA/PPO, PBT/PC/ABSor PBT/PET/PC.

[0231] 30. Naturally occurring and synthetic organic materials which arepure monomeric compounds or mixtures of such compounds, for examplemineral oils, animal and vegetable fats, oil and waxes, or oils, fatsand waxes based on synthetic esters (e.g. phthalates, adipates,phosphates or trimellitates) and also mixtures of synthetic esters withmineral oils in any weight ratios, typically those used as spinningcompositions, as well as aqueous emulsions of such materials.

[0232] 31. Aqueous emulsions of natural or synthetic rubber, e.g.natural latex or latices of carboxylated styrene/butadiene copolymers.

[0233] Thus, the invention also relates to a composition containing anorganic material susceptible to degradation induced by light, heat oroxidation and a compound of the formula (IA) or (IB) as described above.

[0234] The organic material is preferably a synthetic polymer, moreparticularly one selected from the aforementioned groups. The syntheticpolymer is for example a thermoplastic polyolefin (TPO), a thermoplasticelastomer (TPE) or a thermoplastic vulcanizate (TPV).

[0235] Polyolefins are preferred. Thermoplastic polyolefins (TPO) oracrylonitrile-butadiene-styrene (ABS) are also preferred.

[0236] The compounds of the formula (IA) or (IB) are further useful ascorrosion inhibitors and also as light stabilizers for coatings. Thus, afurther preferred embodiment of the present invention relates to acoating containing a compound of the formula (IA) or (IB). Suitablecoatings are for example described in U.S. Pat. No. 6,117,997, column26, line 55 to column 32, line 21.

[0237] Pigmented vulcanized rubbers or pigmented thermoplasticelastomers containing a compound of the formula (IA) or (IB) with theproviso being not applied to the definition of the formula (IA) are aparticularly preferred embodiment of this invention. A pigmented (nonblack) rubber vulcanizate contains for example elastomers, vulcanizingagents, accelerators, accelerator activators, age-resistors,fillers/pigments, softeners and some further miscellaneous ingredients.

[0238] Examples of elastomers are polyisoprene or polybutadiene;copolymers of monoolefins and diolefins with each other or with othervinyl monomers, e.g. ethylene/octene copolymers, propylene/butadienecopolymers, isobutylene/isoprene copolymers, ethylene/alkyl acrylatecopolymers or ethylene/alkyl methacrylate copolymers; terpolymers ofethylene with propylene and a diene such as hexadiene, dicyclopentadieneor ethylidene-norbornene; and mixtures of such copolymers with oneanother and with polymers mentioned above in 1); copolymers of styreneor α-methylstyrene with dienes or acrylic derivatives, for examplestyrene/butadiene, styrene/acrylonitrile, styrene/alkyl methacrylate,styrene/butadiene/alkyl acrylate or styrene/butadiene/alkylmethacrylate; block copolymers of styrene such asstyrene/butadiene/styrene, styrene/isoprene/styrene,styrene/ethylene/butylene/styrene or styrene/ethylene/propylene/styrene;halogen-containing polymers such as polychloroprene, chlorinatedrubbers, chlorinated and brominated copolymer of isobutylene-isoprene(halobutyl rubber) or chlorinated or sulfochlorinated polyethylene;copolymers of the monomers mentioned above under 9) with each other orwith other unsaturated monomers, for example acrylonitrile/butadienecopolymers; polyblends such as PP/EPDM, poly-amide/EPDM or ABS; oraqueous emulsions of natural or synthetic rubber, e.g. natural latex orlatices of carboxylated styrene/butadiene copolymers.

[0239] Vulcanizing agents are chemicals that are required to crosslinkthe rubber chains into the three-dimensional network which gives thedesired physical properties in the final product. The most common agentused is sulfur and sulfur-bearing chemicals (sulfur donors). Examples ofagents which are used for non-sulfur vulcanization are metal oxides, di-or polyfunctional compounds and peroxides.

[0240] Accelerators are generally needed for sulfur-crosslinking. Thesechemicals reduce the time required for vulcanization and improve theproperties of the vulcanizate. Accelerators belong mainly to thefollowing chemical groups: amines (e.g. hexamethylene tetramins),guanidines (e.g. diphenyl guanidine), thioureas, thiazoles, thiurams,sulfenamides or dithiocarbamates.

[0241] Accelerator activators are components used to increase thevulcanization rate by activating the accelerator so that it performsmore effectively. Accelerator activators are for example inorganiccompounds (mainly metal oxides) such as zinc oxide, red lead, magnesiumoxide or alkali carbonates. The most common accelerator activator iszinc oxide. Further, accelerator activators can also be organic acids(normally used in combination with metal oxides) such as high molecularweight monobasic acids or mixtures thereof. Examples are stearic acid,oleic acid, lauric acid, palmitic acid and myristic acid.

[0242] Age-resisters are usually selected from the below-mentioned listof conventional additives.

[0243] Fillers may either reinforce, extend, dilute, or impart certainproperties to rubbers. Carbon black is normally used for blackformulations. For non-black colored formulations, fillers and pigmentsfrom the following classes of mineral fillers can be used: Pyrogenic orprecipitated silica, calcium silicate, calcium carbonate, china clay andhard clay.

[0244] Examples of further miscellaneous ingredients are:

[0245] a) colorants or pigments such as titanium dioxide, zinc oxide,zinc sulfide, iron oxide, Microlen (RTM) Yellow 3G, Microlen (RTM) DPPRed BP, Microlen (RTM) Green GFN, Ciba (RTM) IRGACOLOR (RTM) Yellow2GLMA, Ciba (RTM) IRGACOLOR (RTM) Yellow 2GTM, Ciba (RTM) CROMOPHTAL(RTM) Yellow 8GN, Ciba (RTM) IRGAZIN (RTM) Yellow 2GLTE, Ciba (RTM)IRGALITE (RTM) Yellow WGP, Ciba (RTM) CROMOPHTAL (RTM) Yellow 3G, Ciba(RTM) IRGALITE (RTM) Yellow WSR, Ciba (RTM) IRGALITE (RTM) Yellow BAWP,Ciba (RTM) CROMOPHTAL (RTM) Yellow GR, Ciba (RTM) CROMOPHTAL (RTM)Yellow GT-AD, Ciba (RTM) CROMOPHTAL (RTM) Yellow HRP, Ciba (RTM)CROMOPHTAL (RTM) Yellow 2RF, Ciba (RTM) CROMOPHTAL (RTM) Yellow 2RLTS,Ciba (RTM) CROMOPHTAL (RTM) Yellow 2RLP, Ciba (RTM) IRGAZIN (RTM) Yellow3RLTN, Ciba (RTM) CROMOPHTAL (RTM) Orange 2G, Ciba (RTM) CROMOPHTAL(RTM) DPP Orange TRP, Ciba (RTM) CROMOPHTAL (RTM) Orange GP, Ciba (RTM)IRGALITE (RTM) Orange F2G, Ciba (RTM) IRGAZIN (RTM) DPP Orange RA, Ciba(RTM) CROMOPHTAL (RTM) Brown 5R, Ciba (RTM) CROMOPHTAL (RTM) Scarlet RN,Ciba (RTM) IRGALITE (RTM) Red LCB, Ciba (RTM) IRGALITE (RTM) Red 2BY,Ciba (RTM) CROMOPHTAL (RTM) DPP Flame Red EP, Ciba (RTM) CROMOPHTAL(RTM) Red G, Ciba (RTM) CROMOPHTAL (RTM) DPP Red BOC, Ciba (RTM) IRGAZIN(RTM) DPP Red BO, Ciba (RTM) CROMOPHTAL (RTM) DPP Red BP, Ciba (RTM)CROMOPHTAL (RTM) Red 2030, Ciba (RTM) IRGAZIN (RTM) DPP Red BTR, Ciba(RTM) CROMOPHTAL (RTM) Red BRN, Ciba (RTM) CROMOPHTAL (RTM) Red BN, Ciba(RTM) IRGALITE (RTM) Red 2BSP, Ciba (RTM) IRGAZIN (RTM) DPP Rubine TR,Ciba (RTM) CROMOPHTAL (RTM) Red A3B, Ciba (RTM) CROMOPHTAL (RTM) Red 2B,Ciba (RTM) CROMOPHTAL (RTM) Red 2020, Ciba (RTM) CINQUASIA (RTM) Red YRT-759-D, Ciba (RTM) IRGALITE (RTM) Red 2BP, Ciba (RTM) CINQUASIA (RTM)Red B RT-790-D, Ciba (RTM) IRGALITE (RTM) Rubine 4BP, Ciba (RTM)CINQUASIA (RTM) Red B RT-195-D, Ciba (RTM) CINQUASIA (RTM) MagentaRT-235-D, Ciba (RTM) CINQUASIA (RTM) Violet R RT-891-D, Ciba (RTM)CROMOPHTAL (RTM) Violet B, Ciba (RTM) CROMOPHTAL (RTM) Violet GT, Ciba(RTM) CROMOPHTAL (RTM) Blue A3R, Ciba (RTM) IRGALITE (RTM) Blue BLPO,Ciba (RTM) IRGALITE (RTM) Blue BSP, Ciba (RTM) CROMOPHTAL (RTM) Blue4GNP, Ciba (RTM) IRGALITE (RTM) Blue GBP, Ciba (RTM) IRGALITE (RTM)Green GFNP; b) blowing agents, c) flame retardants, d) retarders, e)odorants, and f) abrasives.

[0246] In pigmented vulcanized rubbers or pigmented thermoplasticelastomers, the compound of the formula (IA) or (IB) is preferablyapplied together with an UV absorber, in particular one of those listedin group 2 of the list of conventional additives further below. Thecombination of one of the compounds of Examples 1 to 6 of this inventionwith ®TINUVIN 213 which is the transesterification product of2-[3′-tert-butyl-5′-(2-methoxycarbonylethyl)-2′-hydroxyphenyl]-2H-benzotriazolewith polyethylene glycol 300 is particularly preferred.

[0247] A further embodiment of this invention is a method forstabilizing an organic material against degradation induced by light,heat or oxidation, which comprises incorporating into said organicmaterial at least one compound of the formula (IA) or (IB) with theproviso being not applied to the definition of the formula (IA).

[0248] The compounds of this invention can be used in variousproportions depending on the nature of the material to be stabilized, onthe end use and on the presence of other additives. In general, it isappropriate to use for example 0.01 to 10% or 0.01 to 5% of the compoundof the formula (IA) or (IB), relative to the weight of-the material tobe stabilized (or the rubber content), preferably 0.05 to 2% or 0.05 to1% or 0.1 to 5% or 0.2 to 3%.

[0249] The compounds of this invention can be added, for example, to thepolymeric materials before, during or after the polymerization orcrosslinking of the said materials. Furthermore, they can beincorporated in the polymeric materials in the pure form or encapsulatedin waxes, oils or polymers.

[0250] In general, the compounds of this invention can be incorporatedin the polymeric materials by various processes, such as dry mixing inthe form of powder, or wet mixing in the form of solutions orsuspensions or also in the form of a masterbatch which contains thecompounds of this invention in a concentration of 2.5 to 25% by weight;in such operations, the polymer can be used in the form of powder,granules, solutions, suspensions or in the form of latices.

[0251] The materials stabilized with the compounds of this invention canbe used for the production of mouldings, films, tapes, monofilaments,fibres, surface coatings and the like; or colored tires, weatheringstrips, gaskets, sealings, roofing membranes, various technical rubberarticles (hose, tubes) or boots.

[0252] If desired, other conventional additives for synthetic polymers,such as antioxidants, UV absorbers, nickel stabilizers, pigments,fillers, plasticizers, corrosion inhibitors and metal deactivators, canbe added to the organic materials containing the compounds of thisinvention.

[0253] Particular examples of said conventional additives are:

[0254] 1. Antioxidants

[0255] 1.1. Alkylated monophenols, for example2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-di-methylphenol,2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol,2,6-di-tert-butyl-4-isobutylphenol, 2,6-dicyclopentyl-4-methylphenol,2-(a-methylcyclohexyl)-4,6-dimethylphenol,2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol,2,6-di-tert-butyl-4-methoxymethylphenol, nonylphenols which are linearor branched in the side chains, for example 2,6-di-nonyl-4-methylphenol,2,4-dimethyl-6-(1′-methylundec-1′-yl)phenol,2,4-dimethyl-6-(1′-methylheptadec-1′-yl)phenol,2,4-dimethyl-6-(1′-methyltridec-1′-yl)phenol and mixtures thereof.

[0256] 1.2. Alkylthiomethylphenols, for example2,4-dioctylthiomethyl-6-tert-butylphenol,2,4-dioctylthiomethyl-6-methylphenol,2,4-dioctylthiomethyl-6-ethylphenol,2,6-di-dodecylthiomethyl-4-nonylphenol.

[0257] 1.3. Hydroquinones and alkylated hydroquinones, for example2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butylhydroquinone,2,5-di-tert-amylhydroquinone, 2,6-diphenyl-4-octadecyloxyphenol,2,6-di-tert-butylhydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole,3,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyphenylstearate, bis(3,5-di-tert-butyl-4-hydroxyphenyl)adipate.

[0258] 1.4. Tocopherols, for example α-tocopherol, β-tocopherol,γ-tocopherol, 8-tocopherol and mixtures thereof (vitamin E).

[0259] 1.5. Hydroxylated thiodiphenyl ethers, for example2,2′-thiobis(6-tert-butyl-4-methylphenol), 2,2′-thiobis(4-octylphenol),4,4′-thiobis(6-tert-butyl-3-methylphenol),4,4′-thiobis(6-tert-butyl-2-methylphenol),4,4′-thiobis(3,6-di-sec-amylphenol),4,4′-bis(2,6-dimethyl-4-hydroxyphenyl)-disulfide.

[0260] 1.6. Alkylidenebisphenols, for-example2,2′-methylenebis(6-tert-butyl-4-methylphenol),2,2′-methylenebis(6-tert-butyl-4-ethylphenol),2,2′-methylenebis[4-methyl-6-(α-methylcyclohexyl)-phenol],2,2′-methylenebis(4-methyl-6-cyclohexylphenol),2,2′-methylenebis(6-nonyl-4-methylphenol),2,2′-methylenebis(4,6-di-tert-butylphenol),2,2′-ethylidenebis(4,6-di-tert-butyl-phenol),2,2′-ethylidenebis(6-tert-butyl-4-isobutylphenol),2,2′-methylenebis[6-(α-methylbenzyl)-4-nonylphenol],2,2′-methylenebis[6-(α,α-dimethylbenzyl)-4-nonylphenol],4,4′-methylenebis(2,6-di-tert-butylphenol),4,4′-methylenebis(6-tert-butyl-2-methylphenol),1,1-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butane,2,6-bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol,1,1,3-tris(5-tert-butyl-4-hydroxy-2-methylphenyl)butane,1,1-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)-3-n-dodecylmercaptobutane,ethylene glycol bis[3,3-bis(3′-tert-butyl-4′-hydroxyphenyl)butyrate],bis(3-tert-butyl-4-hydroxy-5-methyl-phenyl)dicyclopentadiene,bis[2-(3′-tert-butyl-2′-hydroxy-5′-methylbenzyl)-6-tert-butyl-4-methylphenyl]terephthalate,1,1-bis-(3,5-dimethyl-2-hydroxyphenyl)butane,2,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)propane,2,2-bis-(5-tert-butyl-4-hydroxy2-methylphenyl)-4-n-dodecylmercaptobutane,1,1,5,5-tetra(5-tert-butyl-4-hydroxy-2-methylphenyl)pentane.

[0261] 1.7. O-, N- and S-benzyl compounds, for example3,5,3′,5′-tetra-tert-butyl-4,4′-dihydroxydibenzyl ether,octadecyl-4-hydroxy-3,5-dimethylbenzylmercaptoacetate,tridecyl-4-hydroxy-3,5-di-tert-butylbenzylmercaptoacetate,tris(3,5-di-tert-butyl-4-hydroxybenzyl)amine,bis(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)dithioterephthalate,bis(3,5-di-tert-butyl-4-hydroxybenzyl)sulfide,isooctyl-3,5-di-tert-butyl-4-hydroxybenzylmercaptoacetate.

[0262] 1.8. Hydroxybenzylated malonates, for exampledioctadecyl-2,2-bis(3,5-di-tert-butyl-2-hydroxybenzyl)malonate,di-octadecyl-2-(3-tert-butyl-4-hydroxy-5-methylbenzyl)malonate,didodecylmercaptoethyl-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate,bis[4-(1,1,3,3-tetramethylbutyl)phenyl]-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate.

[0263] 1.9. Aromatic hydroxybenzyl compounds, for example1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene,1,4-bis(3,5-di-tert-butyl-4-hydroxybenzyl)-2,3,5,6-tetramethylbenzene,2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)phenol.

[0264] 1.10. Triazine compounds, for example2,4-bis(octylmercapto)-6-(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine,2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine,2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,3,5-triazine,2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,2,3-triazine,1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate,1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurate,2,4,6-tris (3,5-di-tert-butyl-4-hydroxyphenylethyl)-1,3,5-triazine,1,3,5-tris(3,5-di-tert-butyl-4-hydroxy-phenylpropionyl)-hexahydro-1,3,5-triazine,1,3,5-tris(3,5-dicyclohexyl-4-hydroxybenzyl)isocyanurate.

[0265] 1.11. Benzylphosphonates, for exampledimethyl-2,5-di-tert-butyl-4-hydroxybenzylphosphonate,diethyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate,dioctadecyl3,5-di-tert-butyl-4-hydroxybenzylphosphonate,dioctadecyl-5-tert-butyl-4-hydroxy-3-methylbenzylphosphonate, thecalcium salt of the monoethyl ester of3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid.

[0266] 1.12. Acylaminophenols, for example 4-hydroxylauranilide,4-hydroxystearanilide, octylN-(3,5-di-tert-butyl-4-hydroxyphenyl)carbamate.

[0267] 1.13. Esters of β-(3,5-di-tert-butyl-4-hydroxaphenyl)prorpionicacid with mono- or polyhydric alcohols, e.g. with methanol, ethanol,n-octanol, i-octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol,ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethyleneglycol, diethylene glycol, triethylene glycol, pentaerythritol,tris(hydroxyethyl)isocyanurate, N,N′-bis(hydroxyethyl)oxamide,3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol,trimethylolpropane,4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane.

[0268] 1.14. Esters ofβ-(5-tert-butyl-4-hydroxy-3-methylphenyl)propionic acid with mono- orpolyhydric alcohols, e.g. with methanol, ethanol, n-octanol, i-octanol,octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol,1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethyleneglycol, triethylene glycol, pentaerythritol,tris(hydroxyethyl)isocyanurate, N,N′-bis-(hydroxyethyl)oxamide,3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol,trimethylolpropane,4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane;3,9-bis[2-{3-(3-tertbutyl-4-hydroxy-5-methylphenyl)propionyloxy}-1,1-dimethylethyl]-2,4,8,10-tetraoxaspiro[5.5]-undecane.

[0269] 1.15. Esters of β-(3,5-dicyclohexyl-4-hydroxyphenyl)propionicacid with mono- or polyhydric alcohols, e.g. with methanol, ethanol,octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol,1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethyleneglycol, triethylene glycol, pentaerythritol,tris(hydroxyethyl)isocyanurate, N,N′-bis(hydroxyethyl)oxamide,3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol,trimethylolpropane,4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane.

[0270] 1.16. Esters of 3,5-di-tert-butyl-4-hydroxyphenyl acetic acidwith mono- or polyhydric alcohols, e.g. with methanol, ethanol, octanol,octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol,1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethyleneglycol, triethylene glycol, pentaerythritol,tris(hydroxyethyl)isocyanurate, N,N′-bis(hydroxyethyl)oxamide,3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol,trimethylolpropane,4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane.

[0271] 1.17. Amides of 13-(3,5-di-tert-butyl-4-hydroxyphenyl)propionicacid e.g.N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamide,N,N′-bis(3,5-di-tert-butyl-4-hydroxy-phenylpropionyl)trimethylenediamide,N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazide,N,N′-bis[2-(3-[3,5-di-tert-butyl-4-hydroxyphenyl]propionyloxy)ethyl]oxamide(Naugard®XL-1, supplied by Uniroyal).

[0272] 1.18. Ascorbic acid (vitamin C)

[0273] 1.19. Aminic antioxidants, for exampleN,N′-di-isopropyl-p-phenylenediamine,N,N′-di-sec-butyl-p-phenylenediamine,N,N′-bis(1,4-dimethylpentyl)-p-phenylenediamine,N,N′-bis(1-ethyl-3-methylpentyl)-p-phenylenediamine,N,N′-bis(1-methylheptyl)-p-phenylenediamine,N,N′-dicyclohexyl-p-phenylenediamine, N,N′-diphenyl-p-phenylenediamine,N,N′-bis(2-naphthyl)-p-phenylenediamine,N-isopropyl-N′-phenyl-p-phenylenediamine,N-(1,3-dimethylbutyl)-N′-phenyl-p-phenylenediamine,N-(1-methylheptyl)-N′-phenyl-p-phenylenediamine,N-cyclohexyl-N′-phenyl-p-phenylenediamine,4-(p-toluenesulfamoyl)diphenylamine,N,N′-dimethyl-N,N′-di-sec-butyl-p-phenylenediamine, diphenylamine,N-allyidiphenylamine, 4-isopropoxydiphenylamine,N-phenyl-1-naphthylamine, N-(4-tert-octylphenyl)-1-naphthylamine,N-phenyl-2-naphthylamine, octylated diphenylamine, for examplep,p′-di-tert-octyldiphenylamine, 4-n-butyl-aminophenol,4-butyrylaminophenol, 4-nonanoylaminophenol, 4-dodecanoylaminophenol,4-octadecanoylaminophenol, bis(4-methoxyphenyl)amine,2,6-di-tert-butyl-4-dimethylaminomethylphenol,2,4′-diaminodiphenylmethane, 4,4′-diaminodiphenylmethane, N,N,N′,N′-tetra-methyl-4,4′-diaminodiphenylmethane,1,2-bis[(2-methylphenyl)amino]ethane, 1,2-bis(phenylamino)propane,(o-tolyl)biguamide, bis[4-(1′,3′-dimethylbutyl)phenyl]amine,tert-octylated N-phenyl-1-naphthylamine, a mixture of mono- anddialkylated tert-butyl/tert-octyldiphenylamines, a mixture of mono- anddialkylated nonyldiphenylamines, a mixture of mono- and dialkylateddodecyldiphenylamines, a mixture of mono- and dialkylatedisopropyl/isohexyldiphenylamines, a mixture of mono- and dialkylatedtert-butyldiphenylamines, 2,3-dihydro-3,3-dimethyl-4H-1,4-benzothiazine,phenothiazine, a mixture of mono- and dialkylatedtert-butyl/tert-octylphenothiazines, a mixture of mono- and dialkylatedtert-octylphenothiazines, N-allylphenothiazine,N,N,N′,N′-tetraphenyl-1,4-diaminobut-2-ene,N,N-bis(2,2,6,6-tetramethylpiperid-4-yl-hexamethylenediamine,bis(2,2,-6,6-tetramethylpiperid-4-yl)sebacate,2,2,6,6-tetramethylpiperidin-4-one, 2,2,6,6-tetramethylpiperidin-4-ol.

[0274] 2. UV absorbers and light stabilisers

[0275] 2.1.2-(2′-Hydroxyphenyl)benzotriazoles, for example2-(2′-hydroxy-5′-methylphenyl)benzotriazole,2-(3′,5′-di-tert-butyl-2′-hydroxyphenyl)benzotriazole,2-(5′-tert-butyl-2′-hydroxyphenyl)benzotriazole,2-(2′-hydroxy-5′-(1,1,3,3-tetramethylbutyl)phenyl)benzotriazole,2-(3′,5′-di-tert-butyl-2′-hydroxyphenyl)-5-chlorobenzotriazole,2-(3′-tert-butyl-2′-hydroxy-5′-methylphenyl)-5-chlorobenzotriazole,2-(3′-sec-butyl-5′-tert-butyl-2′-hydroxyphenyl)benzotriazole,2-(2′-hydroxy-4′-octyloxyphenyl)benzotriazole,2-(3′,5′-di-tert-amyl-2′-hydroxyphenyl)benzotriazole,2-(3′,5′-bis(α,α-dimethylbenzyl)-2′-hydroxyphenyl)benzotriazole,2-(3′-tert-butyl-2′-hydroxy-5′-(2-octyloxycarbonylethyl)phenyl)-5-chlorobenzotriazole,2-(3′-tert-butyl-5′-[2-(2-ethylhexyloxy)carbonylethyl]-2′-hydroxyphenyl)-5-chlorobenzotriazole,2-(3′-tert-butyl-2′-hydroxy-5′-(2-methoxycarbonylethyl)phenyl)-5-chlorobenzotriazole,2-(3′-tert-butyl-2′-hydroxy-5′-(2-methoxycarbonylethyl)phenyl)benzotriazole,2-(3′-tert-butyl-2′-hydroxy-5′-(2-octyloxycarbonylethyl)phenyl)benzotriazole,2-(3′-tert-butyl-5′-[2-(2-ethylhexyloxy)carbonylethyl]-2′-hydroxyphenyl)benzotriazole,2-(3′-dodecyl-2′-hydroxy-5′-methylphenyl)benzotriazole,2-(3′-tert-butyl-2′-hydroxy-5′-(2-isooctyloxycarbonylethyl)phenylbenzotriazole,2,2′-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-benzotriazole-2-ylphenol];the transesterification product of2-[3′-tert-butyl-5′-(2-methoxycarbonylethyl)-2′-hydroxyphenyl]-2H-benzotriazolewith polyethylene glycol 300; [R—CH₂CH₂—COO—CH₂CH₂₂, whereR=3′-tert-butyl-4′-hydroxy-5′-2H-benzotriazol-2-ylphenyl,2-[2′-hydroxy-3′-(,sa-dimethylbenzyl)-5′-(1,1,3,3-tetramethylbutyl)phenyl]-benzotriazole;2-[2′-hydroxy-3′-(1,1,3,3-tetramethylbutyl)-5′-(α,α-dimethylbenzyl)phenyl]benzotriazole.

[0276] 2.2.2-Hydroxybenzophenones, for example the 4-hydroxy, 4-methoxy,4-octyloxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4,2′,4′-trihydroxyand 2′-hydroxy-4,4′-dimethoxy derivatives.

[0277] 2.3. Esters of substituted and unsubstituted benzoic acids, forexample 4-tert-butylphenyl salicylate, phenyl salicylate, octylphenylsalicylate, dibenzoyl resorcinol, bis(4-tert-butylbenzoyl)resorcinol,benzoyl resorcinol, 2,4-di-tert-butylphenyl3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl3,5-di-tert-butyl-4-hydroxybenzoate, octadecyl3,5-di-tert-butyl-4-hydroxybenzoate, 2-methyl-4,6-di-tert-butylphenyl3,5-di-tert-butyl-4-hydroxybenzoate.

[0278] 2.4. Acrylates, for example ethyl α-cyano-β,β-diphenylacrylate,isooctyl α-cyano-β,β-diphenylacrylate, methyl α-carbomethoxycinnamate,methyl α-cyano-β-methyl-p-methoxycinnamate, butylα-cyano-β-methyl-p-methoxycinnamate, methylα-carbomethoxy-p-methoxycinnamate andN-(β-carbomethoxy-β-cyanovinyl)-2-methylindoline.

[0279] 2.5. Nickel compounds, for example nickel complexes of2,2′-thiobis[4-(1,1,3,3-tetramethylbutyl)phenol], such as the 1:1 or 1:2complex, with or without additional ligands such as n-butylamine,triethanolamine or N-cyclohexyldiethanolamine, nickeldibutyldithiocarbamate, nickel salts of the monoalkyl esters, e.g. themethyl or ethyl ester, of 4-hydroxy-3,5-di-tert-butylbenzylphosphonicacid, nickel complexes of ketoximes, e.g. of2-hydroxy-4-methylphenylundecylketoxime, nickel complexes of1-phenyl-4-lauroyl-5-hydroxypyrazole, with or without additionalligands.

[0280] 2.6. Sterically hindered amines, for examplebis(2,2,6,6-tetramethyl-4-piperidyl)sebacate,bis(2,2,6,6-tetramethyl-4-piperidyl)succinate,bis(1,2,2,6,6-pentamethyl-4-piperidyl)sebacate,bis(1-octyloxy-2,2,6,6-tetramethyl-4-piperidyl)sebacate,bis(1,2,2,6,6-pentamethyl-4-piperidyl)n-butyl-3,5-di-tert-butyl-4-hydroxybenzylmalonate, the condensate of1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinicacid, linear or cyclic condensates ofN,N′-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and4-tert-octylamino-2,6-di-chloro-1,3,5-triazine,tris(2,2,6,6-tetramethyl-4-piperidyl)nitrilotriacetate,tetrakis(2,2,6,6-tetramethyl-4-piperidyl)-1,2,3,4-butanetetracarboxylate,1,1′-(1,2-ethanediyl)-bis(3,3,5,5-tetramethylpiperazinone),4-benzoyl-2,2,6,6-tetramethylpiperidine,4-stearyloxy-2,2,6,6-tetramethylpiperidine,bis(1,2,2,6,6-pentamethylpiperidyl)-2-n-butyl-2-(2-hydroxy-3,5-di-tert-butylbenzyl)-malonate,3-n-octyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione,bis(1-octyloxy-2,2,6,6-tetramethylpiperidyl)sebacate,bis(1-octyloxy-2,2,6,6-tetramethylpiperidyl)succinate, linear or cycliccondensates ofN,N′-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and4-morpholino-2,6-dichloro-1,3,5-triazine, the condensate of2-chloro-4,6-bis(4-n-butylamino-2,2,6,6-tetramethylpiperidyl)-1,3,5-triazineand 1,2-bis(3-aminopropylamino)-ethane, the condensate of2-chloro-4,6-di-(4-n-butylamino-1,2,2,6,6-pentamethylpiperidyl)-1,3,5-triazineand 1,2-bis(3-aminopropylamino)ethane,8-acetyl-3-dodecyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione,3-dodecyl-1-(2,2,6,6-tetramethyl-4-piperidyl)pyrrolidine-2,5-dione,3-dodecyl-1-(1,2,2,6,6-pentamethyl-4-piperidyl)pyrrolidine-2,5-dione, amixture of 4-hexadecyloxy- and4-stearyloxy-2,2,6,6-tetramethylpiperidine, a condensate ofN,N′-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and4-cyclohexylamino-2,6-dichloro-1,3,5-triazine, a condensate of1,2-bis(3-aminopropylamino)ethane and 2,4,6-trichloro-1,3,5-triazine aswell as 4-butylamino-2,2,6,6-tetramethylpiperidine (CAS Reg. No.(136504-96-6]); a condensate of 1,6-hexanediamine and2,4,6-trichloro-1,3,5-triazine as well as N,N-dibutylamine and4-butylamino-2,2,6,6-tetramethylpiperidine (CAS Reg. No. [192268-64-7]);N-(2,2,6,6-tetramethyl-4-piperidyl)-n-dodecylsuccinimide,N-(1,2,2,6,6-pentamethyl-4-piperidyl)-n-dodecylsuccinimide,2-undecyl-7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxo-spiro[4,5]decane, areaction product of7,7,9,9-tetramethyl-2-cycloundecyl-1-oxa-3,8-diaza-4-oxospiro-[4,5]decaneand epichlorohydrin,1,1-bis(1,2,2,6,6-pentamethyl-4-piperidyloxycarbonyl)-2-(4-methoxyphenyl)ethene,N,N′-bis-formyl-N,N′-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine,a diester of 4-methoxymethylenemalonic acid with1,2,2,6,6-pentamethyl-4-hydroxypiperidine,poly[methylpropyl-3-oxy-4-(2,2,6,6-tetramethyl-4-piperidyi)]siloxane, areaction product of maleic acid anhydride-a-olefin copolymer with2,2,6,6-tetramethyl-4-aminopiperidine or1,2,2,6,6-pentamethyl-4-aminopiperidine.

[0281] 2.7. Oxamides, for example 4,4′-dioctyloxyoxanilide,2,2′-diethoxyoxanilide, 2,2′-dioctyloxy-5,5′-di-tert-butoxanilide,2,2′-didodecyloxy-5,5′-di-tert-butoxanilide, 2-ethoxy-2′-ethyloxanilide,N,N′-bis(3-dimethylaminopropyl)oxamide,2-ethoxy-5-tert-butyl-2′-ethoxanilide and its mixture with2-ethoxy-2′-ethyl-5,4′-di-tert-butoxanilide, mixtures of o- andp-methoxy-disubstituted oxanilides and mixtures of o- andp-ethoxy-disubstituted oxanilides.

[0282] 2.8.2-(2-Hydroxyphenyl)-1,3,5-triazines, for example2,4,6-tris(2-hydroxy-4-octyloxyphenyl)-1,3,5-triazine,2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine,2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine,2,4-bis(2-hydroxy-4-propyloxyphenyl)-6-(2,4-dimethylphenyl)-1,3,5-triazine,2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(4-methylphenyl)-1,3,5-triazine,2-(2-hydroxy-4-dodecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine,2-(2-hydroxy-4-tridecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine,2-[2-hydroxy-4-(2-hydroxy-3-butyloxypropoxy)phenyl]-4,6-bis(2,4-dimethyl)-1,3,5-triazine,2-[2-hydroxy-4-(2-hydroxy-3-octyloxypropyloxy)phenyl]-4,6-bis(2,4-dimethyl)-1,3,5-triazine,2-[4-(dodecyloxy/tridecyloxy-2-hydroxypropoxy)-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine,2-[2-hydroxy-4-(2-hydroxy-3-dodecyloxypropoxy)phenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine,2-(2-hydroxy-4-hexyloxy)phenyl-4,6-diphenyl-1,3,5-triazine,2-(2-hydroxy-4-methoxyphenyl)-4,6-diphenyl-1,3,5-triazine,2,4,6-tris[2-hydroxy-4-(3-butoxy-2-hydroxypropoxy)phenyl]-1,3,5-triazine,2-{2-hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazine,2-(2-hydroxy-4-[3-(2-ethylhexyl-1-oxy)-2-hydroxypropyloxy]phenyl}-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine.

[0283] 3. Metal deactivators, for example N,N′-diphenyloxamide,N-salicylal-N′-salicyloyl hydrazine, N,N′-bis(salicyloyl)hydrazine,N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazine,3-salicyloylamino-1,2,4-triazole, bis(benzylidene)oxalyl dihydrazide,oxanilide, isophthaloyl dihydrazide, sebacoyl bisphenylhydrazide,N,N′-diacetyladipoyl dihydrazide, N,N′-bis(salicyloyl)oxalyldihydrazide, N,N′-bis(salicyloyl)thiopropionyl dihydrazide.

[0284] 4. Phosphites and phosphonites, for example triphenyl phosphite,diphenylalkyl phosphites, phenyldialkyl phosphites, tris(nonylphenyl)phosphite, trilauryl phosphite, trioctadecyl phosphite,distearylpentaerythritol diphosphite, tris(2,4-di-tert-butylphenyl)phosphite, diisodecyl pentaerythritol diphosphite,bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite,bis(2,4-dicumylphenyl)pentaerythritol diphosphite,bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite,diisodecyloxypentaerythritol diphosphite,bis(2,4-di-tert-butyl-6-methylphenyl)-pentaerythritol diphosphite,bis(2,4,6-tris(tert-butylphenyl)pentaerythritol diphosphite, tristearylsorbitol triphosphite, tetrakis(2,4-di-tert-butylphenyl)4,4′-biphenylene diphosphonite,6-isooctyloxy-2,4,8,10-tetra-tert-butyl-12H-dibenz[d,g]-1,3,2-dioxaphosphocin,bis(2,4-di-tertbutyl-6-methylphenyl)methyl phosphite,bis(2,4-di-tert-butyl-6-methylphenyl)ethyl phosphite,6-fluoro-2,4,8,10-tetra-tert-butyl-12-methyl-dibenz[d,g]-1,3,2-dioxaphosphocin,2,2′,2″-nitrilo-[triethyltris(3,3′,5,5′-tetra-tert-butyl-1,1′-biphenyl-2,2′-diyl)phosphite],2-ethylhexyl(3,3′,5,5′-tetra-tert-butyl-1,1′-biphenyl-2,2′-diyl)phosphite,5-butyl-5-ethyl-2-(2,4,6-tri-tert-butylphenoxy)-1,3,2-dioxaphosphirane.

[0285] The following phosphites are especially preferred:

[0286] Tris(2,4-di-tert-butylphenyl) phosphite (Irgafos®168,Ciba-Geigy), tris(nonylphenyl) phosphite,

[0287] 5. Hydroxylamines, for example N,N-dibenzylhydroxylamine,N,N-diethylhydroxylamine, N,N-dioctylhydroxylamine,N,N-dilaurylhydroxylamine, N,N-ditetradecylhydroxylamine,N,N-dihexadecylhydroxylamine, N,N-dioctadecylhydroxylamine,N-hexadecyl-N-octadecylhydroxylamine,N-heptadecyl-N-octadecylhydroxylamine, N,N-dialkylhydroxylamine derivedfrom hydrogenated tallow amine.

[0288] 6. Nitrones, for example N-benzyl-alpha-phenylnitrone,N-ethyl-alpha-methylnitrone, N-octyl-alpha-heptyinitrone,N-lauryl-alpha-undecyinitrone, N-tetradecyl-alpha-tridecylnitrone,N-hexadecyl-alpha-pentadecylnitrone,N-octadecyl-alpha-heptadecyinitrone,N-hexadecyl-alpha-heptadecyinitrone,N-ocatadecyl-alpha-pentadecylnitrone,N-heptadecyl-alpha-heptadecyinitrone,N-octadecyl-alpha-hexadecylnitrone, nitrone derived fromN,N-dialkylhydroxylamine derived from hydrogenated tallow amine.

[0289] 7. Thiosynergists, for example dilauryl thiodipropionate ordistearyl thiodipropionate.

[0290] 8. Peroxide scavengers, for example esters of β-thiodipropionicacid, for example the lauryl, stearyl, myristyl or tridecyl esters,mercaptobenzimidazole or the zinc salt of 2-mercaptobenzimidazole, zincdibutyldithiocarbamate, dioctadecyl disulfide, pentaerythritoltetrakis(β-dodecylmercapto)propionate.

[0291] 9. Polyamide stabilisers, for example copper salts in combinationwith iodides and/or phosphorus compounds and salts of divalentmanganese.

[0292] 10. Basic co-stabilisers, for example melamine,polyvinylpyrrolidone, dicyandiamide, triallyl cyanurate, ureaderivatives, hydrazine derivatives, amines, polyamides, polyurethanes,alkali metal salts and alkaline earth metal salts of higher fatty acids,for example calcium stearate, zinc stearate, magnesium behenate,magnesium stearate, sodium ricinoleate and potassium palmitate, antimonypyrocatecholate or zinc pyrocatecholate.

[0293] 11. Nucleating agents, for example inorganic substances, such astalcum, metal oxides, such as titanium dioxide or magnesium oxide,phosphates, carbonates or sulfates of, preferably, alkaline earthmetals; organic compounds, such as mono- or polycarboxylic acids and thesalts thereof, e.g. 4-tert-butylbenzoic acid, adipic acid,diphenylacetic acid, sodium succinate or sodium benzoate; polymericcompounds, such as ionic copolymers (ionomers). Especially preferred are1,3:2,4-bis(3′,4′-dimethylbenzylidene)sorbitol,1,3:2,4-di(paramethyldibenzylidene)sorbitol, and1,3:2,4-di(benzylidene)sorbitol.

[0294] 12. Fillers and reinforcing agents, for example calciumcarbonate, silicates, glass fibres, glass bulbs, asbestos, talc, kaolin,mica, barium sulfate, metal oxides and hydroxides, carbon black,graphite, wood flour and flours or fibers of other natural products,synthetic fibers.

[0295] 13. Other additives, for example plasticisers, lubricants,emulsifiers, pigments, rheology additives, catalysts, flow-controlagents, optical brighteners, flameproofing agents, antistatic agents andblowing agents.

[0296] 14. Benzofuranones and indolinones, for example those disclosedin U.S. Pat. No. 4,325,863; U.S. Pat. No. 4,338,244; U.S. Pat. No.5,175,312; U.S. Pat. No. 5,216,052; U.S. Pat. No. 5,252,643;DE-A-4316611; DE-A-4316622; DE-A-4316876; EP-A-0589839 or EP-A-0591102or 3-[4-(2-acetoxyethoxy)-phenyl]-5,7-di-tert-butylbenzofuran-2-one,5,7-di-tert-butyl-3-[4-(2-stearoyloxyethoxy)phenyl]-benzofuran-2-one,3,3′-bis[5,7-di-tert-butyl-3-(4-[2-hydroxyethoxy]phenyl)benzofuran-2-one],5,7-di-tert-butyl-3-(4-ethoxyphenyl)benzofuran-2-one,3-(4-acetoxy-3,5-dimethylphenyl)-5,7-di-tert-butylbenzofuran-2-one,3-(3,5-dimethyl-4-pivaloyloxyphenyl)-5,7-di-tert-butylbenzofuran-2-one,3-(3,4-dimethylphenyl)-5,7-di-tert-butylbenzofuran-2-one,3-(2,3-dimethylphenyl)-5,7-di-tert-butylbenzofuran-2-one.

[0297] The weight ratio of the compounds of this invention to theconventional additives may be for example 1:0.5 to 1:5.

[0298] Other materials which may be stabilized with the compounds of theformula (IA) or (IB) are recording materials for photographicreproduction and other reprographic techniques as described for examplein Research Disclosure 1990, 31429 (pages 474-480), GB-A-2,319,523 orDE-A-19,750,906, page 22, line 15 to page 105, line 32.

[0299] Thus, another preferred embodiment of this invention is arecording material, in particular a photographic material, containing atleast one compound of the formula (IA) or (IB) with the proviso beingnot applied to the definition of the formula (IA).

[0300] Of special importance is also the stabilization of non-silverreprographic materials, for example, those used for pressure-sensitivecopying systems, microcapsule photocopier systems, heat-sensitive copiersystems and ink-jet printing.

[0301] The recording materials stabilized with the compounds of theformula (IA) or (IB) have an unexpectedly high quality, especially interms of their light stability.

[0302] The recording materials have a structure which is known per seand which corresponds to their utility. They consist of a base, forexample a paper or plastic film, on which one or more coatings areapplied. Depending on the type of the material, these coats contain thesuitable components required. In the case of photographic materials, thecoats contain for example silver halide emulsions, colour couplers, dyesand the like. The material intended for ink-jet printing has e.g. acustomary base on which an absorption layer suitable for ink is located.Uncoated paper can likewise be employed for ink-jet printing. In thelatter case, the paper simultaneously functions as a base and has theabsorbent for the ink. Suitable materials for ink-jet printing aredescribed, inter alia, in U.S. Pat. No. 5,073,448, the disclosurecontent of which is regarded as part of the present description.

[0303] The recording material can also be transparent, for example inthe case of projection films.

[0304] The compound of the formula (IA) or (IB) can be incorporated intothe material even in the course of manufacture; in papermaking, forexample, by addition to the pulp. Another method of use is the sprayingof the material with an aqueous solution of the compound of the formula(IA) or (IB), or the addition thereof to the coating.

[0305] Coatings for transparent recording materials for projection mustnot contain any light-scattering particles such as pigments or fillers.

[0306] The colour-binding coatings can contain further additives, forexample antioxidants, light stabilizers (including UV absorbers and/orconventional hindered amine light stabilizers), viscosity improvers,brighteners, biocides and/or antistats.

[0307] The coating is usually prepared as described in the following.The water-soluble components, for example the binder, are dissolved inwater and mixed. The solid components, for example fillers and otheradditives as already described, are dispersed in this aqueous medium.Dispersion is advantageously brought about with the aid of equipmentsuch as ultrasonic devices, turbine agitators, homogenizers, colloidmills, bead mills, sand mills, high-speed stirrers and the like. Aparticular advantage of the compounds of the formula (IA) or (IB) isthat they can easily be incorporated into the coating.

[0308] As mentioned above, the recording materials cover a broad fieldof use. Compounds of the formula (IA) or (IB) can be employed, forexample, in pressure-sensitive copier systems. They can be added to thepaper to protect the micro-encapsulated dye precursors against light, orto the binder of the developer layer for protecting the dyes formedtherein.

[0309] Photocopier systems with light-sensitive microcapsules which aredeveloped by pressure are described, inter alia, in U.S. Pat. No.4,416,966, U.S. Pat. No. 4,483,912, U.S. Pat. No. 4,352,200, U.S. Pat.No. 4,535,050, U.S. Pat. No. 4,536,463, U.S. Pat. No. 4,551,407, U.S.Pat. No. 4,562,137 and U.S. Pat. No. 4,608,330 and also in EP-A-139,479,EP-A-162,664, EP-A-164,931, EP-A-237,024, EP-A-237,025 and EP-A-260,129.In all these systems, the compounds of the formula (IA) or (IB) can beadded to the colour-accepting layer. Alternatively, the compounds of theformula (IA) or (IB) can be added to the donor layer for protecting thecolour formers against light.

[0310] The compounds of the formula (IA) or (IB) can also be employed inrecording materials which are based on the principle ofphotopolymerization, photosoftening or the rupture of microcapsules, or,when heat-sensitive or photosensitive diazonium salts, leuco dyes withoxidizing agent or colour lactones with Lewis acids are used.

[0311] Heat-sensitive recording material exploits the colour-impartingreaction between a colourless or weakly coloured base dye and an organicor inorganic colour developer; the recorded image being produced byheat-induced contact of the two materials. This type of heat-sensitiverecording material is very widespread, not only as the recording mediumfor faxes, computers, etc., but also in many other fields, for examplein label printing.

[0312] The heat-sensitive recording material according to the presentinvention is composed of a base, a heat-sensitive colour-formingrecording layer on this base, and, optionally, a protective layer on theheat-sensitive, colour-forming recording layer. The heat-sensitive,colour-forming recording layer contains as its principal constituent acolour-imparting compound and a colour-developing compound, and also acompound of the formula (IA) or (IB). If a protective layer is present,the compound of the formula (IA) or (IB) can also be incorporated intothe protective layer.

[0313] Heat-sensitive recording materials are described, for example, inJP-A-Hei 8-267 915.

[0314] Further fields of use are recording materials for dye diffusiontransfer printing, thermal wax transfer printing and dot matrixprinting, and for use with electrostatic, electrographic,electrophoretic, magnetographic and laser-electrophotographic printers,recorders or plotters. Of the materials mentioned, preference is givento recording materials for dye diffusion transfer printing as describedfor example in EP-A-507,734.

[0315] Compounds of the formula (IA) or (IB) can also be employed ininks (preferably for ink-jet printing) for example as described in U.S.Pat. No. 5,098,477, the disclosure content of which is regarded as partof the present description. The invention therefore preferably alsorelates to an ink comprising at least one compound of the formula (IA)or (IB) as stabilizer. The ink, especially for ink-jet printing,contains preferably water. Inks contain the stabilizer of the formula(IA) or (IB) usually in a concentration of from 0.01 to 20% by weight,in particular from 0.5 to 10% by weight.

[0316] The photographic material according to this invention can be ablack and white or can be a colour photographic material. A colourphotographic material is preferred.

[0317] Examples of colour photographic materials are colour negativefilms, colour reversal films, colour positive films, colour photographicpaper, colour reversal photographic paper, colour-sensitive materialsfor the dye diffusion transfer process or the silver dye bleach process.

[0318] Details of the photographic materials to be stabilized accordingto this invention and components which can be employed therein aregiven, inter alia, in GB-A-2,319,523, DE-A-19,750,906, page 23, line 20to page 105, line 32, and U.S. Pat. No. 5,538,840, column 25, line 60 tocolumn 106, line 31. These parts of U.S. Pat. No. 5,538,840 areincorporated herein by way of reference.

[0319] The compounds of this invention can be introduced in any layer ofa silver halide photographic material, however, they are preferablyincorporated in a chromogenic layer, in particular in a layer containinga yellow coupler. They are used, for example, in a 1% to 200% weightratio with the coupler, preferably 1% to 100%. The compounds of thepresent invention can be used in combination with other conventionalstabilizers that can be incorporated in the same layer or in a differentlayer. Examples of suitable conventional stabilizers are described inGB-A-2,319,523, DE-A-19,750,906 and U.S. Pat. No. 5,538,840 and includein particular phenolic stabilizers, conventional hindered aminestabilzers, UV absorbers, preferably those of the hydroxyphenylbenztriazole type or of the hydroxyphenyl triazine class, and the like.

[0320] Examples of yellow couplers are also disclosed in U.S. Pat. No.5,538,840, column 33, line 3 to column 47, line 15.

[0321] Thus, further preferred embodiments of this invention are:

[0322] (1) A photographic material comprising on a substrate at leastone layer containing a compound of the formula (IA) or (IB).

[0323] (2) A silver halide colour photographic material comprising asupport having thereon at least one light-sensitive silver halideemulsion layer and optionally a non-light sensitive emulsion layer,characterized in that at least one light-sensitive layer contains acompound of the formula (IA) or (IB).

[0324] (3) A silver halide colour photographic material comprising asupport having thereon a) at least one cyan-forming unit composed of ared-sensitive silver halide emulsion layer containing a cyan dye-formingcoupler, b) at least one magenta-forming unit composed of agreen-sensitive silver halide emulsion layer containing a magentadye-forming coupler and c) at least one yellow-forming unit composed ofa blue-sensitive silver halide emulsion layer containing a yellowdye-forming coupler, characterized in that

[0325] the blue-sensitive layer contains a compound of the formula (IA)or (IB).

[0326] The invention is illustrated in more detail by the followingExamples. All percentages are by weight, unless otherwise indicated.

EXAMPLE 1 Preparation of the Compound of the Formula

[0327]

[0328] 1.1. Preparation of the Intermediate2,2,5,5-tetramethylimidazolidine-4-thione:

[0329] 525 ml of water, 143 g of NH₄Cl and 106.7 g of Na₂S are placed ina 2 l four necked flask equipped with a mechanical stirrer, thermometer,condenser and gas inlet tube. The solution is stirred for 30 minutes and102 g of acetone are added. During 2 hours at 20/25° C., 85 g of acetonecyanohydrin are added dropwise to the solution obtained. The mixture isleft to react under stirring for additional 2 hours. The suspensionobtained is heated to 60° C. and is stirred for additional 2 hours.Then, the suspension is heated to 85° C. and NH₃ is removed. Thereaction mixture is cooled to 20° C. and a white solid is recovered,washed with 200 ml of water and dried at 30° C. under vacuum.

[0330] 1.2. Preparation of the Intermediate2,2,5,5-tetramethylimidazolidine-4-one:

[0331] 290 g (1.83 mol) of the intermediate of step 1.1 are dissolved inwater. Then, 183 g of NaOH are added. The solution is cooled to 5° C.and 893 g of a water solution of 35% (w/w) of H₂O₂ is slowly added.After adding, the mixture is heated at room temperature. The solution pHis corrected to 8 with acetic acid and the water is removed. Then, 1 lof dichloromethane is added and the salts are filtered off. The organicsolution is dried under anhydrous sodium sulphate and evaporated undervacuum.

[0332] 1.3. Preparation of the Intermediate of the Formula

[0333] 132 g (1.16 mol) of potassium tert-butoxide are slowly added to asuspension of 168 g (1.18 mol) of the intermediate of step 1.2 in 500 mlof anhydrous toluene. After the addition, 131 g (0.54 mol) of1.6-dibromohexane are added. The mixture is left to react for 4 hoursand then washed twice with water. The organic layer is dried underanhydrous sodium sulphate and then evaporated under vacuum.

[0334] 1.4. Preparation of the Intermediate of the Formula

[0335] A mixture of 138 g (0.38 mol) of the intermediate of step 1.3,121.5 g (1 mol) of allyl bromide and 140 g (1 mol) of potassiumcarbonate in 500 ml of toluene is poured into an autoclave. The mixtureis heated at 145° C. for 10 hours. Then, the mixture is washed twicewith 250 ml of water, the organic layer is separated, dried under sodiumsulphate and evaporated under vacuum. The product obtained is a yellowpowder with a visual melting range of 82-87° C.

[0336] 1.5. Preparation of the Final Product:

[0337] The mixture of 44 g (0.099 mol) of the intermediate of step 1.4and 130 g (1.24 mol) of sodium carbonate in 150 ml of toluene is cooledat −5° C. and a solution of 35% (w/w) of per-acetic acid in acetic acid(23 g, 0.30 mol) is slowly added. After the addition, the mixture isleft to react for additional 2 hours at −5° C. and then additional 30hours at room temperature. Subsequently, the mixture is washed twicewith 50 ml of water, the organic layer is separated, dried under sodiumsulphate and evaporated under vacuum. A pale yellow oil is obtained.

[0338]¹H NMR (300 MHz, CDCl₃): δ 5.84-5.73 (m, 2H); 5.15-5.02 (m, 4H);4.18-4.16 (m, 4H); 2.99 (t, 4H); 1.44-1.37 (m, 8H); 1.13 (s, 12H);1.06-1.01 (s, 12H).

EXAMPLE 2 Preparation of the Compound of the Formula

[0339]

[0340] 0.5 g of Pt on carbon (5% w/w) are added to a solution of 30 g(0.063 mol) of the compound of EXAMPLE 1 in 120 ml of methanol. Then,the mixture is poured into an autoclave and hydrogenated for 4 hours at20 bar (H₂ pressure) and 30° C. The mixture is filtered off and thesolution is concentrated under vacuum. The product obtained is a yellowpowder with a visual melting range of 60-67° C.

EXAMPLE 3 Preparation of the Compound of the Formula

[0341]

[0342] 3.1. Preparation of the Intermediate of the Formula

[0343] 341 g (4.1 mol) of sodium carbonate and 433 g (13.53 mol) ofmethanol are added dropwise to a suspension of 250 g (1.35 mol) ofcyanuric chloride in 500 ml of xylene. The mixture is left to react at35° C. for about 70 hours. Then, the mixture is filtered off toeliminate the salts and the solution is evaporated under vacuum. The rowmaterial is crystallized from n-octane.

[0344] 3.2. Preparation of the Final Product:

[0345] 41 g (0.35 mol) of potassium tert-butoxide are slowly added to asuspension of 55 g (0.39 mol) of the intermediate of EXAMPLE 1, step 1.2in 200 ml of toluene. After the addition, the mixture is left to reactat 40° C. for about 1 hour. Vacuum is inserted and always at 40° C. 100ml of solution are distilled off. Then, the solution is cooled to 20°C., 100 ml of toluene are added again and 62 g (0.35 mol) of theintermediate of EXAMPLE 1, step 1.2 are slowly added. After theaddition, the mixture is left to react for additional 2 hours and then40 ml of water are added. The organic layer is separated, washed twicewith water, dried on anhydrous sodium sulphate, and evaporated undervacuum. The raw material is crystallized from a mixture of 35 ml oftoluene and 35 ml of n-octane. The product obtained is a white powderwith a visual melting range of 80-88° C.

EXAMPLE 4 Preparation of the Compound of the Formula

[0346]

[0347] 4.1. Preparation of the Intermediate of the Formula

[0348] 34.16 g (0.74 mol) of formic acid are slowly added to asuspension of 70 g (0.44 mol) of the compound of EXAMPLE 1, step 1.2 in100 ml of tert-amyl alcohol. The temperature is increased to 60° C. and8.5 g of formic aldehyde are added. The mixture is left to react for onehour at 75° C. and then, further 8.5 g of formic aldehyde are added. Themixture reacts for additional three hours. After cooling, 300 ml ofdichloromethane are added and after half an hour the organic layer isseparated, washed twice with water, dried over anhydrous sodium sulphateand evaporated under vacuum. The raw material is purified bycrystallization from n-hexane. A white solid is obtained.

[0349] 4.2. Preparation of the Final Product:

[0350] Following the procedure reported in EXAMPLE 3, step 3.2 and usingas starting material the intermediate of step 1, the final product isobtained as a white powder with a visual melting 3 range of 81-87° C.

EXAMPLE 5 Preparation of the Compound of the Formula

[0351]

[0352] 5.1. Preparation of the Intermediate of the Formula

[0353] A solution of 75 g (0.41 mol) of cyanuric chloride in 250 ml ofTHF (tetrahydrofuran) is slowly added to a mixture of 45 g (0.61 mol) ofn-butanol and 50 g (0.59 mol) of sodium carbonate in 100 ml of THF. Themixture is left to react overnight at 40° C. Then, it is filtered onclay in order to eliminate the salts. The organic solution is evaporatedunder vacuum.

[0354] 5.2. Preparation of the Final Product:

[0355] Following the procedure described in EXAMPLE 3, step 3.2 andusing as starting materials the intermediates of EXAMPLE 4 step 4.1 andEXAMPLE 5, step 5.1, the final product is obtained as a white powderwith a visual melting range of 121-128° C.

EXAMPLE 6 Preparation of the Compound of the Formula

[0356]

[0357] 6.1. Preparation of the Intermediate of the Formula

[0358] Following the procedure described in EXAMPLE 5, step 5.1 andusing iso-propanol as starting material, a pale yellow oil is obtained.

[0359] 6.2. Preparation of the Final Product:

[0360] Following the procedure described in EXAMPLE 3, step 3.2 andusing as starting materials the intermediates of EXAMPLE 1, step 1.2 andEXAMPLE 6, step 6.1, the final product is obtained as a white powderwith a visual melting range of 181-186° C.

[0361] Compounds of the Formula (IA) or (IB) used as Stabilizers in theFollowing Application Examples:

EXAMPLE A-1 Stabilization of a Red Pigmented and Sulfur Crosslinkedethylene-propylene-diene-elastomer (EPDM)

[0362] Recipe in parts by weight: EPDM (Buna ® AP 451) 100.0 Silica(Ultrasil ® VN 3) 30.0 Paraffin oil (Naftolen ® ND) 20.0 Stearic acid1.0 ZnO 3.0 Carbowax 2.0 TiO₂ 2.0 4,6-Bis{octylthiomethyl}-o-cresol 0.5Sulfur 1.5 Vulkacit ® CZ/C 1.0 Vulkacit ® Thiuram MS 0.8 PigmentMicrolen ® Red MO 3302 0.5 Light Stabilizer (see Table A-1) 1.0

[0363] The components of the recipe are mixed at 70° C. in an open rollmill. For incorporation of the pigment, the temperature is raised to110C. The cure time at 160° C. is determined in a MDR 2000 rheometer.

[0364] 2 mm plates are cured at 160° C. until t₉₅ of the rheometer curve(minutes to 95% of the rheometer curve maximum).

[0365] The rubber samples are exposed to artificial light in an ATLAS®Cl 1200 Weather-O-meter without water spray. The ΔE is periodicallydetermined according to ASTM D 1925-70. The results are indicated inTable A-1. TABLE A-1 Light Stabilizer ΔE after 1000 hours *) Without 11Stabilizer 1 7.4

EXAMPLE A-2 Stabilization of a Green Pigmented and Sulfur Crosslinkedethylene-propylene-diene-elastomer (EPDM)

[0366] Recipe in parts by weight: EPDM (Buna ® AP 451) 100.0 Silica(Ultrasil ®  VN 3) 30.0 Paraffin oil (Ingraplast ® SRSS) 20.0 Stearicacid 1.0 ZnO 3.0 Carbowax 2.0 TiO₂ 2.0 4,6-Bis{octylthiomethyl}-o-cresol0.5 Sulfur 1.5 Vulkacit ® CZ/C 1.0 Vulkacit ® Thiuram MS 0.8 PigmentMicrolen ® Green MO 177 0.5 Light Stabilizer (see Table A-2) 1.0

[0367] The components of the recipe are mixed at 70° C. in an open rollmill. For incorporation of the pigment, the temperature is raised to110° C. The cure time at 160° C. is determined in a MDR 2000 rheometer.

[0368] 2 mm plates are cured at 160° C. until T₉₅ of the rheometer curve(minutes to 95% of the rheometer curve maximum).

[0369] The rubber samples are exposed to artificial light in an ATLAS®Cl 1200 Weather-O-meter without water spray. The AE is periodicallydetermined according to ASTM D 1925-70. The results are indicated inTable A-2. TABLE A-2 Light Stabilizer ΔE after 1000 hours *) Without 20Stabilizer 1 7.4 Stabilizer 2 11

EXAMPLE A-3 Stabilization of a Yellow Pigmented and Sulphur Crosslinkedstyrene-butadiene-copolymer (SBR)

[0370] Recipe in parts by weight: ® ESBR 1709 (® Enichem) 100.0 ZnO 5.0Stearic acid 1.0 ® Winnofil/ICI (white filler) 50.0 Pigment ® MicroleneYellow MOO 138 3G 0.5 TIO₂ (Rutile) 3.0 Sulphur 2.0 ® Vulkacit DM(® Bayer) 1.5 ® Vulkacit D (® Bayer) 0.5 Light Stabilizer (see TableA-3) 1.6

[0371] The components of the recipe and the stabilizer listed in TableA-3 are mixed at 70° C. in an open roll mill. For incorporation of thepigment, the temperature is raised to 110° C.

[0372] The cure time at 130° C. is determined in a MDR 2000 rheometer.

[0373] 2 mm plates are cured at 130° C. until T₉₅ of the rheometer curve(minutes to 95% of the rheometer curve maximum).

[0374] The rubber samples are exposed to artificial light in an ®AtlasCl 1200 Weather-O-meter without water spray. The Yellowness-Index (ΔLand Δa) is determined periodically according to ASTM D 1925-70. Theresults are indicated in Table A-3. TABLE A-3 Light Stabilizer ΔL after500 hours Δa after 500 hours Without −11  11.6 Stabilizer 3 −8 9.2Stabilizer 4 −4 6.1

EXAMPLE B-1 Stabilization of Photographic Layers

[0375] Chromogenic photographic layers are prepared by coating agelatine emulsion containing silver bromide, a yellow coupler and anadditive on a polyethylene-coated paper.

[0376] The composition of the layers is as given in the following table(all amounts in mg/m²): Component Amount in the layer Gelatine 5150 AgBr 520 Yellow coupler Coup Y1 769 Coupler solvent Solv1 256 Additive(Table B-1) 231 Hardener Ha1 300 Surfactant Su1 340

[0377] The layers are dried for 7 days in a ventilated cabinet.

[0378] The dried samples are exposed to white light through a step wedgeof 0.3 log E exposure steps and then developed with Agfa's P94 processfor colour negative papers, following manufacturer's recommendations.

[0379] After exposure and processing, the remission density of theyellow dye is measured in the blue channel. The samples are then exposedin an Atlas Weatherometer so as to receive 60 kJ/cm² light energy. Thetemperature is 43° C. and the relative humidity 50%. The density lossstarting from a density of 1 is determined. TABLE B-1 Density loss (%)Additive (initial density = 1) None 46 Stabilizer 5 17

[0380] The above table shows that Stabilizer 5 according to the presentinvention improves the light stability of the yellow dye.

EXAMPLE C-1 Stabilization of Polypropylene Blue Plaques

[0381] 1 g of Stabilizer 2 (solubilized in the minimum amount ofacetone), 1 g of calcium stearate and 1 g of Blue ®Filofin G are mixedin a turbomixer with 1000 g of polypropylene ®Montell JE 6100 powderwhich contains 835 ppm of tris(2,4-di-tert-butylphenyl) phosphite and355 ppm of pentaerythritoltetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate) and which hasa melt index of 3 g/10 min (measured at 230° C. and 2.16 Kg).

[0382] The mixture is extruded at a maximum temperature of 230° C. usinga ®Berstoff extruder, to give polymer granules, which are subsequentlyconverted to plaques 2 mm thick, using an injection molding machine®Negri-Bossi, Italy) and working at a maximum temperature of 220° C.

[0383] The plaques thus prepared are mounted on a white card and exposedin a Weather-O-Meter ®Atlas Ci65A (ASTM G26, continuous exposure tolight without water spray) with a black panel temperature of 63° C. andrelative humidity of 30%.

[0384] The degree of chalking and superficial roughness are measured, asan evaluation of surface degradation, on samples taken after variouslight exposure times. A numeric scale, where 10 is the top value for thenon exposed (not degraded) sample is adopted to rank the degree ofchalking of the samples. Roughness is measured with a “Surtronic 3+”.

[0385] By way of comparison, a plaque prepared under the same conditionsas indicated above, but without the addition of the stabilizer of thepresent invention, is exposed.

[0386] The results obtained are shown in Table 1. TABLE 1 *) Hours of *)Hours of Weather-O-Meter Weather-O-Meter exposure Stabilizer exposure tochalking to 0.50 μm roughness —  600  348 Stabilizer 2 2600 2678

1. A compound of the formula (IA) or (IB)

wherein G₁, G₂, G₃ and G₄ are independently of one another C₁-C₁₈alkylor C₅-C₁₂cycloalkyl or the radicals G₁ and G₂ and the radicals G₃ and G₄form independently of one another, together with the carbon atom theyare attached to, C₅-C₁₂cycloalkyl; R is C₁-C₁₈alkyl, C₁-C₁₈hydroxyalkyl,C₂-C₁₈alkenyl, C₅-C₁₂cycloalkyl, C₇-C₁₂phenylalkyl unsubstituted orsubstituted on the phenyl radical by C₁-C₄alkyl and/or C₁-C₄alkoxy; orC₁-C₁₈alkanoyl; R* is hydrogen, C₁-C₁₈alkyl, oxyl, —OH, —CH₂CN,C₃-C₆alkenyl, C₃-C₈alkynyl, C₇-C₁₂phenylalkyl unsubstituted orsubstituted on the phenyl radical by C₁-C₄alkyl and/or C₁-C₄alkoxy;C₁-C₈acyl, C₁-C₁₈alkoxy, C₁-C₁₈hydroxyalkoxy, C₂-C₁₈alkenyloxy,C₅-C₁₂cycloalkoxy, C₇-C₁₂phenylalkoxy unsubstituted or substituted onthe phenyl radical by C₁-C₄alkyl and/or C₁-C₄alkoxy; C₁-C₁₈alkanoyloxy,(C₁-C₁₈alkoxy)carbonyl, glycidyl or a group, —CH₂CH(OH)(G) with G beinghydrogen, methyl or phenyl; n is 1, 2, 3 or 4; n* is 1, 2 or 3; X is anorganic radical of a valency equal to n; when n* is 1, X* is a group ofthe formula (IB-1)

wherein Z₁* and Z₂* are independently of one another —O— or >N—R₃*; R₁*,R₂* and R₃* are independently of one another hydrogen, C₁-C₁₈alkyl,C₃-C₁₈alkenyl, C₅-C₁₂cycloalkyl which is unsubstituted or substituted byC₁-C₄alkyl and/or C₁-C₄alkoxy; or C₇-C₉phenylalkyl which isunsubstituted or substituted on the phenyl radical by C₁-C₄alkyl and/orC₁-C₄alkoxy; when n* is 2, X* is a group of the formula (IB-2)

wherein Z₁* and R₁* are as defined above; when n* is 3, X* is a group ofthe formula (IB-3);

when n is 2, 3 or 4, each of the radicals G₁, G₂, G₃, G₄ and R can havethe same or a different meaning in the units of the formula

when n* is 2 or 3, each of the radicals G₁, G₂, G₃, G₄ and R* can havethe same or a different meaning in the units of the formula

with the proviso that when n is 1, R is methyl, ethyl, propyl,C₁-C₁₈hydroxyalkyl, C₂-C₁₈alkenyl, C₅-C₁₂cycloalkyl or C₁-C₁₈alkanoyl.2. A compound of the formula (IA) according to claim 1 wherein when n is1, X is C₂-C₁₈alkyl, C₂-C₁₈hydroxyalkyl, C₂-C₁₈alkyl interrupted byoxygen, sulphur or >N—R₀ with R₀ being as defined below; C₂-C₁₈alkenyl,C₂-C₁₈alkynyl, C₅-C₁₂cycloalkyl unsubstituted or substituted by —OH,C₁-C₄alkyl and/or C₁-C₄alkoxy; phenyl or C₇-C₉phenylalkyl unsubstitutedor substituted on the phenyl radical by —OH, C₁-C₄alkyl and/orC₁-C₄alkoxy; or X is one of the groups of the formulae (II-a) to (II-m)

Y₁, Y₂, Y₅, Y₆, Y₇ and Y₉ are a direct bond, C₁-C₁₂alkylene,C₅-C₁₂cycloalkylene or phenylene; Y₃, Y₄, Y₈, Y₁₀, Y₁₁ and Y₁₂ areC₂-C₁₂alkylene, C₅-C₁₂cycloalkylene or phenylene; R₁, R₂, R₃, R₄, R₅,R₆, R₇ and R₁₃ are hydrogen, C₁-C₁₈alkyl, C₂-C₁₈alkyl interrupted byoxygen, sulphur or >N—R₀ with R₀ being as defined below; C₂-C₁₈alkenyl,C₂-C₁₈alkynyl, C₅-C₁₂cycloalkyl unsubstituted or substituted byC₁-C₄alkyl and/or C₁-C₄alkoxy; phenyl unsubstituted or substituted byC₁-C₄alkyl and/or C₁-C₄alkoxy; or C₇-C₉phenylalkyl unsubstituted orsubstituted on the phenyl radical by C₁-C₄alkyl and/or C₁-C₄alkoxy; Z₁,Z₂ and Z₃ are independently of one another —O— or >N—R₁₆; R₀, R₈, R₉,R₁₀, R₁₁, R₁₂, R₁₄, R₁₅ and R₁₆ are independently of one anotherhydrogen, C₁-C₁₈alkyl, C₃-C₁₈alkenyl, C₅-C₁₂cycloalkyl which isunsubstituted or substituted by C₁-C₄alkyl and/or C₁-C₄alkoxy; orC₇-C₉phenylalkyl which is unsubstituted or substituted on the phenylradical by C₁-C₄alkyl and/or C₁-C₄alkoxy; with the proviso that theformula (II-b) is different from ethoxycarbonyl; when n is 2, X isC₂-C₁₂alkylene, C₂-C₁₆alkylene interrupted by oxygen, sulphur or >N—R₀′with R₀′ being as defined below; C₂-C₁₂alkenylene, C₂-C₁₂alkynylene,C₅-C₁₂cycloalkylene,C₅-C₁₂cycloalkylene-(C₁-C₄alkylene)-C₅-C₁₂cycloalkylene,C₁-C₄alkylene-(C₅-C₁₂cycloalkylene)-C₁-C₄alkylene, phenylene,phenylene-(C₁-C₄alkylene)-phenylene orC₁-C₄alkylene-phenylene-C₁-C₄alkylene, or X is one of the groups of theformulae (III-a) to (III-j)

Y₁′, Y₁″, Y₂′, Y₂″, Y₅′, Y₅″, Y₆′, Y₆″, Y₇′ and Y₇″ are independently ofone another a direct bond, C₁-C₁₂alkylene, C₅-C₁₂cycloalkylene orphenylene; Y₃′, Y₃″, Y₄′, Y₄″, Y₈′, Y₈″, Y₁₁′, Y₁₁″, Y₁₂′ and Y₁₂″ areindependently of one another C₂-C₁₂alkylene, C₅-C₁₂cycloalkylene orphenylene; A₁, A₂, A₃, A₄, A₅, A₆, A₇, A₈ and A₉ are C₂-C₁₂alkylene,C₂-C₁₂alkylene interrupted by oxygen, sulphur or >N—R₀′ with R₀′ beingas defined below, C₂-C₁₂alkenylene, C₂-C₁₂alkynylene,C₅-C₁₂cycloalkylene,C₅-C₁₂cycloalkylene-(C₁-C₄alkylene)-C₅-C₁₂cycloalkylene,C₁-C₄alkylene-(C₅-C₁₂cycloalkylene)-C₁-C₄alkylene, phenylene,phenylene-(C₁-C₄alkylene)-phenylene orC₁-C₄alkylene-phenylene-C₁-C₄alkylene; and A₁ and A₅ are additionally adirect bond; Z₁′, Z₂′ and Z₃′ are independently of one another —O— or>N—R₁₆′; and R₀′, R₁₄′ and R₁₆′ are independently of one anotherhydrogen, C₁-C₁₈alkyl, C₃-C₁₈alkenyl, C₅-C₁₂cycloalkyl which isunsubstituted or substituted by C₁-C₄alkyl and/or C₁-C₄alkoxy; orC₇-C₉phenylalkyl which is unsubstituted or substituted on the phenylradical by C₁-C₄alkyl and/or C₁-C₄alkoxy: when n is 3, X isC₅-C₂₅alkantriyl, C₄-C₁₈triacyl or a group of the formula (IV);

Y₁₃′, Y₁₃″ and Y₁₃′″ are independently of one another C₂-C₁₂alkylene,C₅-C₁₂cycloalkylene or phenylene; Z₁″, Z₂″ and Z₃″ are independently ofone another —O— or >N—R₁₆″; and R₁₆″ is hydrogen, C₁-C₁,alkyl,C₃-C₁₈alkenyl, C₅-C₁₂cycloalkyl which is unsubstituted or substituted byC₁-C₄alkyl and/or C₁-C₄alkoxy; or C₇-C₉phenylalkyl which isunsubstituted or substituted on the phenyl radical by C₁-C₄alkyl and/orC₁-C₄alkoxy; and when n is 4, X is C₅-C₂₀alkantetrayl, C₆-C₂₂tetraacylor a group of the formula (V)

Y₁₄′ and Y₁₄″ are independently of one another C₂-C₁₂alkylene,C₅-C₁₂cycloalkylene or phenylene; Z₁′″, Z₂′″, M and T are independentlyof one another —O— or >N—R₁₆′″, and M and T are additionally —S—; R₁₆′″is hydrogen, C₁-C₁₈alkyl, C₃-C₁₈alkenyl, C₅-C₁₂cycloalkyl which isunsubstituted or substituted by C₁-C₄alkyl and/or C₁-C₄alkoxy; orC₇-C₉phenylalkyl which is unsubstituted or substituted on the phenylradical by C₁-C₄alkyl and/or C₁-C₄alkoxy; and q is an integer from 2 to12.
 3. A compound according to claim 1 wherein G₁, G₂, G₃ and G₄ aremethyl.
 4. A compound of the formula (IA) according to claim 1 wherein Ris C₁-C₁₂alkyl, C₁-C₁₂hydroxyalkyl, C₂-C₈alkenyl or C₅-C₈cycloalkyl. 5.A compound of the formula (IA) according to claim 1 wherein R is propyl,C₁-C₁₂hydroxyalkyl, C₂-C₈alkenyl or C₅-C₈cycloalkyl.
 6. A compound ofthe formula (IB) according to claim 1 wherein R* is hydrogen,C₁-C₄alkyl, oxyl, —OH, C₃-C₆alkenyl, benzyl, C₁-C₈acyl, C₁-C₁₂alkoxy,C₁-C₁₂hydroxyalkoxy, C₂-C₈alkenyloxy or C₅-C₈cycloalkoxy.
 7. A compoundof the formula (IA) according to claim 1 wherein R is methyl, propyl,butyl, octyl, hydroxybutyl, 2-propenyl or cyclohexyl.
 8. A compound ofthe formula (IB) according to claim 1 wherein R* is hydrogen, methyl,allyl, acetyl, methoxy, propoxy, butoxy, octyloxy, hydroxybutoxy,2-propenyloxy or cyclohexyloxy.
 9. A compound of the formula (IA)according to claim 1 wherein n is
 2. 10. A compound according to claim 2wherein when n is 1, X is C₂-C₁₂alkyl, C₂-C₁₂hydroxyalkyl, C₂-C₁₂alkylinterrupted by oxygen or >N—R₀ with R₀ being as defined below;C₂-C₁₈alkenyl, C₅-C₈cycloalkyl unsubstituted or substituted byC₁-C₄alkyl; or benzyl unsubstituted or substituted on the phenyl radicalby —OH and/or C₁-C₄alkyl; or X is one of the groups of the formulae(II-a) to (II-m); Y₁, Y₂, Y₅, Y₆, Y₇ and Y₉ are a direct bond,C₁-C₆alkylene, cyclohexylene or phenylene; Y₃, Y₄, Y₈, Y₁₀, Y₁₁, and Y₁₂are C₂-C₆alkylene, cyclohexylene or phenylene; R₁, R₂, R₃, R₄, R₅, R₆,R₇ and R₁₃ are hydrogen, C₁-C₁₂alkyl, C₂-C₁₂alkyl interrupted by oxygenor >N—R₀ with R₀ being as defined below; C₂-C₁₈alkenyl, C₅-C₈cycloalkylunsubstituted or substituted by C₁-C₄alkyl; phenyl unsubstituted orsubstituted by C₁-C₄alkyl; or benzyl unsubstituted or substituted on thephenyl radical by C₁-C₄alkyl; Z₁, Z₂ and Z₃ are independently of oneanother —O— or >N—R₁₆; R₀, R₈, R₉, R₁₀, R₁₁, R₁₂, R₁₄, R₁₅ and R₁₆ areindependently of one another hydrogen, C₁-C₁₂alkyl, C₃-C₁₈alkenyl,C₅-C₈cycloalkyl which is unsubstituted or substituted by C₁-C₄alkyl; orbenzyl unsubstituted or substituted on the phenyl radical by C₁-C₄alkyl;with the proviso that the formula (II-b) is different fromethoxycarbonyl; when n is 2, X is C₂-C₆alkylene, C₂-C₁₆alkyleneinterrupted by oxygen or >N—R₀′ with R₀″ being as defined below;C₂-C₆alkenylene, cyclohexylene,cyclohexylene-(C₁-C₄alkylene)-cyclohexylene,C₁-C₄alkylene-cyclohexylene-C₁-C₄alkylene orC₁-C₄alkylene-phenylene-C₁-C₄alkylene, or X is one of the groups of theformulae (III-a) to (III-j); Y₁′, Y₁″, Y₂′, Y₂″, Y₅′, Y₅″, Y₆′, Y₆″, Y₇′and Y₇″ are independently of one another a direct bond, C₁-C₆alkylene,cyclohexylene or phenylene; Y₃′, Y₃″, Y₄′, Y₄″, Y₈′, Y₈″, Y₁₁ 40 , Y₁₁″,Y₁₂′ and Y₁₂″ are independently of one another C₂-C₆alkylene,cyclohexylene or phenylene; A₁, A₂, A₃, A₄, A₅, A₆, A₇, A₈ and A₉ areC₂-C₆alkylene, C₂-C₆alkylene interrupted by oxygen or >N—R₀′ with R₀′being as defined below, C₂-C₆alkenylene, cyclohexylene,cyclohexylene-(C₁-C₄alkylene)-cyclohexylene,C₁-C₄alkylene-cyclohexylene-C₁-C₄alkylene orC₁-C₄alkylene-phenylene-C₁-C₄alkylene; and A₁ and A₅ are additionally adirect bond; Z₁′, Z₂′ and Z₃′ are independently of one another —O— or>N—R₁₆′; and R₀′, R₁₄′ and R₁₆′ are independently of one anotherhydrogen, C₁-C₁₂alkyl, C₃-C₁₈alkenyl, C₅-C₈cycloalkyl which isunsubstituted or substituted by C₁-C₄alkyl; or benzyl which isunsubstituted or substituted on the phenyl radical by C₁-C₄alkyl; when nis 3, X is C₅-C₁₀alkantriyl, an aliphatic C₄-C₁₈triacyl, an aliphaticO₆—C₁₈triacyl substituted by nitrogen; a cycloaliphatic C₆-C₁₈triacyl,an aromatic C₉-C₁₈triacyl, a heterocyclic C₉-C₁₈triacyl or a group ofthe formula (IV); Y₁₃′, Y₁₃″ and Y₁₃′″ are independently of one anotherC₂-C₆alkylene, cyclohexylene or phenylene; Z₁″, Z₂″ and Z₃″ areindependently of one another —O— or >N—R₁₆″; and R₁₆″ is hydrogen,C₁-C₁₂alkyl, C₃-C₁₈alkenyl, C₅-C₈cycloalkyl which is unsubstituted orsubstituted by C₁-C₄alkyl; or benzyl which is unsubstituted orsubstituted on the phenyl radical by C₁-C₄alkyl; and when n is 4, X isC₁₅-C₁₈alkantetrayl, an aliphatic C₆-C₁₈tetraacyl, an aliphaticC₁₀-C₁₈tetraacyl substituted by nitrogen, a cycloaliphaticC₁₀-C₂₂tetraacyl, an aromatic C₁₀-C₁₈tetraacyl or a group of the formula(V); Y₁₄′ and Y₁₄″ are independently of one another C₂-C₆alkylene,cyclohexylene or phenylene; Z₁′″, Z₂′″, M and T are independently of oneanother —O— or >N—R₁₆′″, and M and T are additionally —S—; R₁₆′″ ishydrogen, C₁-C₁₂alkyl, C₃-C₁₈alkenyl, C₅-C₈cycloalkyl which isunsubstituted or substituted by C₁-C₄alkyl; or benzyl which isunsubstituted or substituted on the phenyl radical by C₁-C₄alkyl; and qis an integer from 2 to
 12. 11. A compound according to claim 2 whereinwhen n is 1, X is C₂-C₆alkyl, C₂-C₆hydroxyalkyl, C₂-C₆alkyl interruptedby oxygen; allyl, cyclohexyl, benzyl or one of the groups of theformulae (II-a) to (II-l); Y₁, Y₂, Y₅, Y₆, Y₇ and Y₉ are a direct bond,C₁-C₆alkylene, cyclohexylene or phenylene; Y₃, Y₄, Y₈, Y₁₀, Y₁₁, and Y₁₂are C₂-C₆alkylene, cyclohexylene or phenylene; R₁, R₂, R₃, R₄, R₅, R₆,R₇ and R₁₃ are hydrogen, C₁-C₈alkyl, C₂-C₆alkyl interrupted by oxygen;allyl, cyclohexyl, phenyl or benzyl; Z₁, Z₂ and Z₃ are independently ofone another —O— or >N—R₁₆; R₀, R₈, R₉, R₁₀, R₁₁, R₁₂, R₁₄, R₁₅ and R₁₆are independently of one another hydrogen, C₁-C₆alkyl, allyl, cyclohexylor benzyl; with the proviso that the formula (II-b) is different fromethoxycarbonyl; when n is 2, X is C₂-C₆alkylene, C₂-C₁₄alkyleneinterrupted by oxygen or >N—R₀′; cyclohexylene or one of the groups ofthe formulae (III-a) to (III-j); Y₁′, Y₁″, Y₂′, Y₂″, Y₅′, Y₅″, Y₆′, Y₆″,Y₇′ and Y₇″ are independently of one another a direct bond,C₁-C₆alkylene, cyclohexylene or phenylene; Y₃′, Y₃″, Y₄′, Y₄″, Y₈′, Y₈″,Y₁₁′, Y₁₁″, Y₁₂′ and Y₁₂″ are independently of one anotherC₂-C₆alkylene, cyclohexylene or phenylene; A₁, A₂, A₃, A₄, A₅, A₆, A₇,A₈ and A₉ are C₂-C₆alkylene, C₂-C₆alkylene interrupted by oxygen;cyclohexylene or phenylene; and A₁ and A₅ are additionally a directbond; Z₁′, Z₂′ and Z₃′ are independently of one another —O— or >N—R₁₆′;and R₀′, R₁₄′ and R₁₆′ are independently of one another hydrogen,C₁-C₆alkyl, allyl, cyclohexyl or benzyl: when n is 3, X is a group ofthe formula (IV); Y₁₃′, Y₁₃″ and Y₁₃′″ are independently of one anotherC₂-C₆alkylene, cyclohexylene or phenylene; Z₁″, Z₂″ and Z₃″ areindependently of one another —O— or >N—R₁₆″; and R₁₆″ is hydrogen,C₁-C₆alkyl, allyl, cyclohexyl or benzyl; and when n is 4, X is a groupof the formula (V); Y₁₄′ and Y₁₄″ are independently of one anotherC₂-C₆alkylene, cyclohexylene or phenylene; Z₁′″, Z₂′″, M and T areindependently of one another —O— or >N—R₁₆′″; R₁₆′″ is hydrogen,C₁-C₆alkyl, allyl, cyclohexyl or benzyl; and q is an integer from 2 to12.
 12. A compound according to claim 2 wherein when n is 2, X isC₂-C₆alkylene or C₂-C₁₄alkylene interrupted by oxygen or >N—R₀′; or X isa group of the formula (III-a), (III-b) or (III-j).
 13. A compound ofthe formula (IA) according to claim 1 wherein G₁, G₂, G₃ and G₄ aremethyl; R is C₁-C₁₂alkyl, C₁-C₁₂hydroxyalkyl, C₂-C₈alkenyl orC₅-C₈cycloalkyl; when n is 1, X is a group of the formula (II-a) or(II-l);

Y₁ is a direct bond or C₁-C₆alkylene; R₁ is C₁-C₈alkyl; Z₁, Z₂ and Z₃are >N—R₁₆; R₁₄, R₁₅ and R₁₆ are independently of one another hydrogenor C₁-C₆alkyl; and Y₁₂ is C₂-C₆alkylene; when n is 2, X isC₂-C₆alkylene, C₂-C₁₄alkylene interrupted by 2>N—H; or a group of theformula (III-b) or (III-j);

Y₂′, Y₂″, Y₁₂′ and Y₁₂″ are independently of one another C₁-C₆alkylene;A₂ is C₂-C₆alkylene; Z₁′, Z₂′ and Z₃′ are independently of one another>N—R₁₆′; and R₁₄′ and R₁₆′ are independently of one another hydrogen orC₁-C₆alkyl; when n is 3, X is a group of the formula (IV);

Y₁₃′, Y₁₃″ and Y₁₃′″ are independently of one another C₂-C₆alkylene;Z₁″, Z₂″ and Z₃″ are a group >N—H; and when n is 4, X is a group of theformula (V);

Y₁₄′ and Y₁₄″ are independently of one another C₂-C₆alkylene; Z₁′″,Z₂′″, M and T are a group >N—H; and q is an integer from 2 to
 6. 14. Acompound of the formula (IA) according to claim 1 wherein G₁, G₂, G₃ andG₄ are methyl; R is propyl or 2-propenyl; n is 2; X is C₂-C₆alkylene ora group of the formula (III-b);

Y₂′ and Y₂″ are independently of one another C₁-C₆alkylene; and A₂ isC₂-C₆alkylene.
 15. A compound of the formula (IA) according to claim 1wherein n is 2, 3 or
 4. 16. A compound of the formula (IA) according toclaim 1, which corresponds to the formula


17. A compound of the formula (IA) according to claim 1, whichcorresponds to the formula


18. A compound of the formula (IB) according to claim 1, wherein G₁, G₂,G₃ and G₄ are methyl; R* is hydrogen, C₁-C₄alkyl, C₁-C₈alkoxy,C₃-C₈alkenyloxy or C₅-C₈cycloalkoxy; n* is 1 or 2; Z₁* and Z₂* are —O—or >N—R₃*; and R₁*, R₂* and R₃* are independently of one anotherhydrogen, C₁-C₆alkyl, allyl, cyclohexyl or benzyl.
 19. A compound of theformula (IB) according to claim 1, wherein G₁, G₂, G₃ and G₄ are methyl;R* is hydrogen or C₁-C₄alkyl; n* is 1 or 2; Z₁* and Z₂* are —O—; and R₁*and R₂* are independently of one another C₁-C₆alkyl.
 20. A compound ofthe formula (IB) according to claim 1, which corresponds to the formula


21. A composition containing an organic material susceptible todegradation induced by light, heat or oxidation and a compound of theformula (IA) or (IB) according to claim
 1. 22. A composition accordingto claim 21, which additionally contains a conventional additive.
 23. Acomposition according to claim 21 wherein the organic material is asynthetic polymer.
 24. A composition containing a pigmented vulcanizedrubber and a compound of the formula (IA) or (IB) according to claim 1with the proviso being not applied to the definition of the formula(IA).
 25. A composition containing a polyolefin and a compound of theformula (IA) or (IB) according to claim 1 with the proviso being notapplied to the definition of the formula (IA).
 26. A compositionaccording to claim 21 wherein the organic material is a thermoplasticpolyolefin (TPO) or acrylonitrile-butadiene-styrene (ABS).
 27. Acomposition containing a thermoplastic polyolefin (TPO) oracrylonitrile-butadiene-styrene (ABS) and a compound of the formula (IA)or (IB) according to claim 1 with the proviso being not applied to thedefinition of the formula (IA).
 28. A recording material containing acompound of the formula (IA) or (IB) according to claim 1 with theproviso being not applied to the definition of the formula (IA).
 29. Amethod for stabilizing an organic material against degradation inducedby light, heat or oxidation, which comprises incorporating into saidorganic material a compound of the formula (IA) or (IB) according toclaim 1 with the proviso being not applied to the definition of theformula (IA).